Unexpected
by Danni1989
Summary: Prequel to Expecting the Unexpected. Everything that happens before Elena gets pregnant in ETU. Elena Gilbert is the popular sophomore cheerleader, Damon Salvatore is the popular but anti-popular junior. What happens when their paths cross? DELENA.
1. The Game

Okay, so here it is, the first chapter of the prequel to "Expecting the Unexpected." I hope you all enjoy it. The next chapter is about half written so it won't be too long of a wait.

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ELENA POV

"Ugh look at him... he's such a... such a... manwhore." I said searching for the appropriate word that described the devil known as Damon Salvatore. Damon Salvatore. He was a junior whereas I was a sophomore not that I had any reason to think about us together in any way. I hated him, he was a pig.

"Yes, he is but you know that any girl in this school would ignore his reputation to roll around in his bed with him." My best friend Caroline Forbes told me.

"It's disgusting. You'll never find me being one of those girls. Ever. I'm serious Care." I told her as she raised her eyebrows at me. Like every other girl in the school he did affect me. I would be lying if I said he didn't. But what set me apart from other girls in this school is that I had no intention of doing anything about those urges. I refused to join the ranking of the school's sluttiest by sleeping with Damon Salvatore, no matter how hot he is.

"Alright, alright. Let's just get practising." Caroline said stopping me before I went on my customary rant about Damon Salvatore and his band of idiots.

"Oh what, so we can enjoy having those assholes stare at us the entire time?" I asked shaking my head. I didn't know why I was in such a bad mood right now. Sure I'd been single for quite a while by now after Matt and I broke up, but that wasn't why. Matt and I stayed really good friends which was rare for an ex couple. And, so far today Damon "the manwhore" Salvatore hadn't tried to hit on me, so really I shouldn't be grumpy.

"If that's how they get their kicks then fine. You're the only girl I know that doesn't like that senior guys are watching us practice." Caroline shrugged.

"Alright, alright." I said going to stand in my position and wait for Caroline to give the cue.

"So are you letting me on the squad yet?" My long time arch-nemesis demanded as she walked up to us just before Caroline gave us the cue to go through the routine for the first time today.

"Not a chance Sophia. We don't like you and you don't like us. Since it's my squad, I figure it's my decision to keep you out." Caroline told her. Caroline knew how much I hated Sophia, so she made it her own personal mission to ensure that she never came near our squad. Best. Friend. Ever.

"Fine. You know eventually you will realize that you need me more than I need you." She hissed before walking away towards Damon and his group.

"Out of all the bad decisions she's ever made, flirting with them is one of the worst." I said of her walking towards the table near where we were practising.

"In her defence, which I never do by the way, they are hot. If they weren't so vile and repulsive I would probably be over there with her. Well not with her, but you know.." Caroline trailed off. Damon's group consisted of himself, Klaus Mikealson, Harper, and Mason Lockwood. They where the school's bad-asses and trouble makers which made them the most popular group in school besides us. The cheerleaders and jocks were popular for being popular and Damon and friends were anti-popular essentially. I hated each and every one of them.

"If they had a good personality to go with their looks, then maybe I could stand them. But they don't so I can't." I said as I gestured for Caroline to get back into formation and to give us the cue to get going on practice.

I watched over my shoulder as Sophia planted herself on their table and was insistently flirting with Damon. He looked mildly interested as he turned his head to face her with that stupid smirk on his face. She grinned at him and leaned in to whisper something in his ear. His smirk widened and I shook my head in response. He was such a pig. Not that I cared what happened to Sophia but even I could see that he wasn't actually into her. He was just pretending for the sake of getting laid. That's how Damon Salvatore worked. He would say whatever he had to say to charm his way into a girls pants. Then he would deny it and ignore the fact that he said it when he proceeded to ignore you for the rest of time since he had gotten what he wanted out of you. Damon Salvatore was one of the worst guys I had ever met but instead of associating with him in any way, I opted to just ignore him. I wanted nothing to do with him and that's the way I chose to live my life until he graduated. "Only two more years Elena. Only two more years." I told myself often.

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DAMON POV

I half ignored Sophia Reynolds as I watched the cheerleaders practice only a few meters from where we sat. I only heard half of what she said but I knew if I wanted to get laid tonight I would have to figure out a way to be more attentive to her. She was the only possible conquest at this time, but she was one I'd had too many times to count. She was good for a quick lay and not much more. She was definitely no fun to talk to, but it was her body that kept me civil to her. She was good in bed and she was willing to do whatever it took to please me. Most girls were but Sophia had the looks to back it up. And bonus, she didn't care that I was using her. Well either she didn't care, or she chose to not believe that was what was happening. Either way it wasn't my problem. I'm an expert and not showing commitment to people, perks of living in a commitment-free household. Commitment is more Stefan's thing than mine.

"Damon... stop watching them. You're supposed to be paying attention to me." Sophia sulked next to me and I fought the urge to roll my eyes. I glanced over my right should and caught my best bud Klaus's expression. He rolled his eyes and I shook my head. Klaus didn't quite understand my need to keep Sophia hanging on. He's all for using a girl for casual sex, it's just his standards are much higher than mine. He would never go for a girl that annoys the hell out of him like Sophia. But she has a hot body and talented mouth so I don't care. I just tend to ignore every single thing she says, which admittedly gets me in trouble sometimes but I don't really care. I ignore her, she gets pissed and walks away for a few days. Then she comes back and gets back into my bed or the backseat of my car, wherever I feel like it. Sometimes I even defile her in her bed at home. That's always fun, since Sophia Reynolds is the daughter of Mrs. Reynolds Mystic Falls High's bitchiest English teacher.

"Damon... you're not listening to me." She whined in her keening little girls voice. I hated her voice so much and this time I really did roll my eyes.

"I'm not... oh well." I said as she wrapped her arms around my bicep and slide herself closer to me. She was wearing a

"Damon approved" short skirt and tank top. I could see enough skin to get her kicked out of school which is what I like. I like it when a girl breaks the rules just to show me what I want to see. It's nice having that kind of power over the female species.

"Damon... I wanted to ask you something." She said grabbing my face and turning me to face her. She leaned in and kissed me dirtily, and if she wanted me to agree to something that was the way to start.

"What do you want?" I sighed. I was fairly easy, bribe me with sex and I would go easy.

"So you know how we've been seeing each other for a while now." She started talking and I almost spit out the coke I had just drunk. Seeing each other? That's what she was calling it now.

"Seeing each other?" I questioned.

"Yeah. We're seeing each other. I'm not seeing anyone else and I don't think you are either. I rock your world much too good for that." She smirked.

"Where are you going with this, so I can say no and we can be done with it." I said trying to rush her along.

"Do you have to be such an ass. But fine, you win. I want you to come home with me and officially meant my parents. They've been dying to meet the guy I'm totally into right now." Sophia told me and my eyes widened.

"I don't know about you, but this is just sex to me. There is nothing more to it. I have no intentions of going to meet your parents. I'm not your boyfriend and I never will be." I told her not caring that I was being overly harsh. She needed to understand the rules. The rules were plain and simple... no boyfriend/girlfriend things. Meeting the parents definitely fell under that heading. She was the last girl I would ever pick to be my girlfriend, if I ever decided that I needed one of those. In my limited understanding of the subject, you had to at least like the girl who was your girlfriend and the only thing I ever felt for Sophia was lust and even that was fading.

"Why are you so awful Damon?" She asked getting off of the table and stalking away from the table.

"Phew you diffused that bomb successfully Salvatore.." Mason told me clapping me on the shoulder. I sighed and grinned at him.

"Was there any chance that I wouldn't?" I asked smirking widely again.

"Nope, I wasn't worried. If you keep that up, she's going to have your children named by next month." Mason joked.

"Which is why I need to let her go, at least temporarily. She needs to get over that stupid crush she has on me. It won't work out well for either of us. If she starts thinking she has some claim on me, it'll make getting other dates much harder." Damon noted as he cupped his chin in his hands.

"Yeah, what we need to find you is a temporary replacement for her, so she knows that she too is replaceable." Mason pondered.

"Meh that won't be too hard for me to find."Damon shrugged as he turned back to the cheerleader show on the grass in front of him.

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**ELENA POV**

"So, are we almost done here today?" I asked Caroline before I took a long drink of water and tugged my shirt down so it covered the maximum amount of skin it possibly could.

"Yep. So what's on the agenda tonight?" Caroline asked as she pulled her sweater on over her shirt and picked up her bag.

"My mom is out of town for the night and Jeremy is heading to one of his friends houses. So I'm meeting my dad for dinner at the Grill. We try to do that at least once a month just the two of us. It keeps him up to speed on my life." I told her. Sue me, I actually enjoy spending time with my parents. I actually like my parents and it doesn't matter to me that people my age are supposed to dislike their parents. I'm the one that actually enjoys their company.

"Cool. So I'll see you tomorrow?" She asked.

"Yep. I'll be here as I am every time there is a practice." I told her.

"Good. I will see you tomorrow Elena." Caroline said.

"You too. Call me tonight if you're bored. We're due for some girl talk soon." I told her and she nodded her head enthusiastically.

"Yes we sure are." She said before heading out in the direction of her car. I followed a couple of minutes behind her, needing to make sure I had all my stuff before heading to my SUV.

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**DAMON POV**

"I love cheerleaders man. They're so...cheery." Mason cheered as the last cheerleader left the grass.

"If you had to pick a cheerleader to fuck... which one would you pick?"Damon asked idly. He was curious about that answer, he hadn't actually slept with a cheerleader yet and he was eager to. He just wasn't sure which one would make the best temporary replacement.

"I don't know dude. I like them all. I would like to have a cheerleader orgy." Mason decided.

"Klaus?" I asked. Although I knew his answer already. He'd been making the same set of googly eyes at the same girl for a long time now. I think it was time he got over that immature infatuation.

"Caroline Forbes. She is like a ray of sunshine in a dreary dark world." Klaus said with a grin.

"Klaus, watch it your corniness is coming out. Careful, you're starting to sound like a pussy." Damon said laughing.

"Having crushes on chicks isn't a bad thing Damon. You'd find it would be good for you." Klaus told him and Damon laughed.

"There is no way in hell having a relationship of any sort would be good for me. I've never seen a functional one so I don't plan on attempting to have one." I told them because it was true. I'd never seen a functional relationship and I probably never would.

"So what's yours?" Mason asked referring to the cheerleader I would like to fuck.

"Now don't judge me... but I want Elena Gilbert." I told them and they all laughed. "

"Shit man, she's a virgin. I heard her tell Blondie that she wasn't ready to give it up that's why she and the Wonder Jock she was dating before broke up." Mason laughed.

"Yeah why the hell do you think I want her?" Damon demanded.

"Oh so you just want another notch on your bedpost. Well good luck with that buddy. Guys like us don't get to fuck girls like her." Mason told him.

"Want a bet? I bet I could get her in my bed or the backseat of my car in one date." I told them. I was completely comfortable in my ability and not even Elena Gilbert would be able to stop me from getting what I want.

"Put your money where your mouth is Salvatore. It's never going to happen in a million years." Mason laughed.

"Damon do you think it's wise that you're betting money on this? What if she finds out, she'd be really hurt?" Klaus asked frowning. He was all for things like this, but he also didn't want to see his dream girls best friend hurt because of his best friend. It would lessen his chances even more with the beautiful Caroline Forbes.

"Yep. It'll be easy because it won't take any effort from me at all to get her into my bed. She's a virgin, so all she probably wants is to get rid of that pesky virginity. I'm more than willing to do that for her, while at the same time make it clear to Sophia that I am not hers." I told them as more of my plan fell into place.

"Well good luck with that. I bet you twenty bucks that you can't get her to sleep with you within a week." Mason gambled.

"I'll bet twenty that I can." Damon said and the two guys shook hands.

"You better get to work." Mason told him grinning. He clearly thought that Damon had no chance in hell of winning this bet.

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I sat down at my fathers and my usual table and waited for him to show up. He had texted me saying that he was running a little late but that he would be here soon. That was my father for you, he was Mystic Falls, resident family physician and he was incredibly busy. But he always made time for me and Jeremy and of course our mother. He was the perfect family man, and it may mean that he spent a lot of time tired, but he was an amazing father.

"Well hello there." A voice that I hated that I recognized sounded through the restaurant.

"Can I help you?" I asked him as he took the seat that my father would soon be occupying.

"Actually yeah, you can go on a date with me." He told me smirking at me. I couldn't believe it, Damon Salvatore was asking me on a date. It was laughable to say the least. I couldn't believe he was that delusional!

"Oh my God, you're not serious are you?" I asked him trying to control laughter.

"I'm dead serious. You know we would have an awesome time together." He told me laying it on thick.

"I'm not interested." I said to him oping he would get the hint and leave me alone.

"Sure you are. I can see that you're attracted to me. Just give it up now." He told me and I glared at him.

"I think you're in my seat." My father's voice interrupted and I was instantly relieved to hear my father standing at the table.

"Yes sir. I was actually just asking your daughter out on a date." Damon said and I rolled my eyes. He knew how to handle parents, that much was clear.

"She's clearly not interested. So you can run along now." Grayson Gilbert said and Damon wisely walked away.

"Thank you daddy." I told him graciously.

"You're welcome sweetie. So now what was that about?" He asked cautiously.

"I don't know. He seems to think I'm going to be his new flavour of the month or something stupid like that. Which is so not going to happen." I told him.

"That's my girl." My dad said patting my hand. Little did I know that was just the beginning.


	2. Let the Games Begin

**Here's the second installment of the prequel. I hope you all enjoy it. Thank you for the generous response to the first chapter. It means a lot that you all like it so far.**

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**Elena POV]**

"Oh my God, Care, you'll never guess what happened tonight at the Grill with me dad." I gasped when I remembered what I was going to tell my best friend.

"What happened?" Caroline asked always ready for more gossip or drama to fill her life. Caroline loved her gossip and whatever she could get her hands on was great to her. It didn't matter who it pertained to, even if it was about one of her best friends.

"You'll never guess who showed up at the Grill while I was having dinner with my dad." I probed her. I loved making her work for her gossip, especially when it was about me essentially.

"Who? Don't leave me hanging here Lena." Caroline pleaded with me.

"Damon Salvatore." I told her knowing it would leave her confused.

"And why is that breaking high school news?" Caroline asked me an irritated lilt to her voice. She was clearly expecting something a whole lot more juicy.

"It's breaking news because he asked me out." I told her and I could practically see Caroline's jaw drop. She gasped and I patted myself on the back. I had finally managed to shock Caroline Forbes, it was a good feeling.

"What did you just say?" Caroline asked me.

"Damon asked me out." I repeated, the sentence leaving a nasty taste in my mouth.

"Oh my God. What did you say?" She asked me.

"I said no of course." I said shocked that she would even have to ask.

"Oh yeah, I guess you would say no." Caroline said deadpan.

"And you're saying you wouldn't?" I asked her.

"One date wouldn't kill anyone. Besides I'm sure he would do it really well. He'd probably pull out all the stops since he's always planning on getting into his dates pants." Caroline reminded me.

"A good date isn't worth how worthless I would feel if I actually went out with him. He's not my type and he never will be. I can't stand the arrogant asshole." I said.

"Well you gotta know that he's not going to give up that fast. If he asked you out, there's got to be a reason for it. If he wants you, he's not going to give up until he's got you." Caroline warned me.

"Well then I'm just going to have to get really good at saying no to assholes like him." I said and Caroline giggled.

"I wish you luck. Besides it'll be fine. How far do you really think he'll go to get you to date him?" Caroline asked.

"I don't know. It's never taken him much effort to get a girl to date him before. Hopefully he'll give up quick" I said.

"Yeah. But I better go. I have a ton of math homework and Mr. Mathis is going to kill me if I don't do it again." Caroline said and I could picture her rolling her eyes.

"Yeah. I can smell popcorn downstairs which means there is a movie night going on. I'm going to go join in on that." I said. Caroline and I said goodbye and then we both hung up. I stood up and pushed my computer chair back into place. I was practically obsessive compulsive about keeping my room clean. A messy bedroom was one of those things that drove me mad. I absolutely hated going into my brother Jeremy's room because it was so messy. When I left my room, I shut the door behind me and walked downstairs.

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**Damon POV**

"Well admittedly that didn't go as well as I'd hoped." I muttered as I sat on the couch in Klaus's living room playing PlayStation on his big screen TV.

"She turned you down?" Klaus asked.

"Yeah, but don't worry. She will go on a date with me. I have no doubt about that. I will be the one to pop her cherry. By the way my miniature failure tonight does not leave this room." I warned my friend.

"Don't worry. I don't relish the idea of listening to Mason brag over you failing. This will not leave the room. And besides I have no doubt that you'll get the girl in the end. I just hope that it doesn't screw up my chances with Caroline Forbes." Klaus said clapping him on the back.

"I will do my best to ensure that I don't burn that bridge for you." Damon promised his friend.

"You'd better. I'm not letting your stupid desire to pop her cherry to ruin my chances with the beautiful blonde goddess." Klaus spoke firmly and I laughed.

"Careful, your lovestruck idiot is coming out again." I laughed.

"Shut up. At least I have someone I want for more than a night." Klaus scoffed.

"But that doesn't stop you from sleeping around like the rest of us. You're just nicer about it." I told him.

"True. Until Caroline notices me, I'm not going to be celibate. Nothing is worth that shit." Klaus said shaking his head.

"Boys, watch your language." Klaus's mom Esther called from the kitchen.

"Yes, ma'am." Damon saluted her, causing the older woman to smile.

"Klaus you too. Be more like Damon please and thank-you." She said.

"Yeah Klaus be more like me. God, I wish I could just live here. Your parents are far better than mine." I sighed knowing at some point I would have to go home.

"Your dad's pretty cool. He just doesn't involve himself too much in your life. Your mom is a piece of work though." Klaus said.

"Yeah, but I should probably get home. I do have homework to complete." He said getting up and pulling his leather jacket

on.

"Oh yeah bad-ass extraordinaire Damon Salvatore goes home to do homework. You're quite odd Salvatore." Klaus teased

him.

"Not my problem I was bred with ambitions. I'm sure as hell not staying here for the rest of my life. I'm going to become hotshot lawyer who has no issues with getting laid every night." I said as I pulled my car keys out of my pocket.

"Good luck with that." Klaus said as I started walking away.

A little while later when I was walking in the front door, the house quiet since my mom was on one of her Italian art gathering trips. What she called art buying, I called Italian artist gathering. She always came home with a new flavour every single time she came home. It drove me crazy how my dad just accepted it.

"Where have you been?" My dad asked from the living room where he was watching a "Criminal Minds" marathon with Stefan.

"Klaus's." I shrugged as I walked towards the stairs.

"Your mother called. She wants you to fly out to meet her. She found some female artists that are in need of your attention apparently." He told me.

"Well tell her the same thing you tell her every time she asks. I have no intention of being an art playboy. No fucking thank you." I said.

"Why would that life be any different than the one you already lead?" Stefan asked snidely.

"Well at least if I do it here then I can torment you much more successfully." I responded.

"I'm glad I asked. So I have good news." Stefan enthused with a wide smile on his face.

"What's going on on, son?" My dad asked him.

"I finally talked to Elena Gilbert today at lunch. She even smiled at me." He said grinning.

"Wow! You talked to Elena Gilbert. I'm so proud of you." I said sarcastically before heading to the stairs.

"Good for you son. I know you've liked her for a long time. Go after what you want." Giuseppe said to Stefan and I chuckled. Stefan had no chance against me, but he just didn't know that I was in it to win it too.

The next morning I got up and jumped into the shower, pulling out all the stops to make myself look hotter than usual. Not that that was possible anyways. I always looked good enough to hear the thud of panties dropping every time I walked past a girl. But no, today this was for one girl. One girl who actually had the gall to turn me down. She had no idea what was coming for her now. She wouldn't be able to deny me for too long. It never worked for long and soon enough I would break her down enough to get her to go out with me. Then it would be easy from then on. All I would have to do is dazzle her with my with and charm then she would be in my bed before the date was done. It was that easy. It always was. I walked downstairs and even Stefan looked more put together than usual. In his case that meant a few more bottles of hair product littering his way over done hair and what looked like a new hoodie.

"Wow Stef, did you buy a new hoodie to impress the girl?" I asked snidely.

"It never hurts to look good." Stefan muttered.

"How many bottles of hair product did you go through today? I'm guessing six." I said laughing. My dad was already gone

for work so he wouldn't yell at me for teasing Stefan.

"Just shut up Damon. I don't need this today." He sighed as he munched on a couple slices of toast with peanut butter and jam.

"Oooh broodier than usual too. Must be nervous to talk to the girl again." I faked sympathy.

"Just leave Damon. Shouldn't you be heading to your band of miserable outcasts?" Stefan muttered and I chuckled.

"How long did it take you to come up with that one. By the way I think you might have competition for Elena Gilbert." I told him. I didn't want him to think I just swooped in and stole his girl, because after-all it was inevitable. I wanted to make my intentions clear.

"Who might that be Damon?" Stefan sighed in his "I'm bored of talking to you Damon" tone of voice.

"Me." I said before walking to the door and shutting it behind me. I figured I'd give him a few hours to stew that over in his head. It would make for a much more entertaining explosion after school.

When I got to school instead of immediately going to join Klaus and the guys on the other side of the quad I took the long way around so I could check out Elena. I needed to gauge her mood for the day so I could decide how I wanted to play this. I could be overly sweet and charming, offering to carry her books for her. Almost all girls loved that side of me that I could turn on just like that. Or I could be sexy and flirty. That was more my default setting than anything, but I could be whatever I had to be to get into bed. On time I sympathized with a girl after her puppy died that she was in the backseat of my car within fifteen minutes. That was a record that I was clearly not going to break with Elena. But sometimes a challenge was fun. When I walked past her, purposely brushing her back when I walked past. She glared at me but immediately went back to chatting happily with her friends.

"Sorry Elena." I said as I walked past and she didn't respond. She was really throwing me off my game, I had no idea what kind of mood she was in. She was happy when I wasn't around but when I was she was glaring daggers at me. It honestly felt like she wanted to set me on fire with her gaze alone.

When I joined the guys Mason nudged me

"So how's it going with our favourite virgin?" He asked me and I shrugged.

"Pretty good. I'm playing it cool right now. She's knows I'm interested now I'm just waiting for her to come to me." I told him even though it was a lie. I had no idea how I was going to get her to go out with me. But like I said before I loved a challenge.

"Is she as easy as the other conquests you've ever had?" Mason asked.

'Admittedly no. But that's fine because I'll still win. She's a little more frosty than I'm used to." I shrugged.

"Good luck. But I just have a feeling I'm going to be twenty bucks richer." Mason said and I shook my head confidently.

"Not going to happen. Sorry buddy." I said just as Sophia came sauntering across the quad.

"Good morning baby. I'm giving you a chance to apologize for your behaviour yesterday." She said sitting down beside me with her hand on my thigh.

"I have nothing to apologize for. I've just been doing what I've been doing the entire time. I never told you it was going to be something that it never will be." I told her bored.

"Come on Damon. Apologize. If you do, I'll make it good for you." She hinted and I rolled my eyes.

"Sorry Soph, but I've got my eyes on something else right now." I told her and her eyes flared.

"You're looking for someone else?" She asked.

"Always. You don't honestly think I'm faithful to you, do you?" I asked her.

"You're supposed to be." She muttered embarrassed.

"That's not how this works Sophia. I fuck you whenever I feel like it and sometimes when you feel like it. And then nothing. We don't date. We don't spend time together and I certainly don't meet your parents." I told her. I was honestly bored of having this conversation over and over again. I just hoped this entire thing with Elena worked out well so she could be my new Sophia until I got bored of her too.

When the bell rang I got up and walked towards the school leaving Sophia sitting at the table with the guys. I subtly followed Elena to her locker and casually bumped into her, needing an opening to talk to her.

"Hey!" She screeched when she fell and dropped her books on the floor.

"Sorry about that." I said in my most apologetic tone as I leaned down to help her pick up her books.

"You did that on purpose. Why won't you just leave me alone? I'm not your type." She told me in almost a pleading tone.

"Nope. You struck my fancy my dear. Just accept a date with me and I'll leave you alone." I told her.

"No. Just give it up so you don't get rejected more times that your fragile little ego can handle." She told me and I chuckled.

"I like you. You're kinda snarky." I said as I handed her the books I made her drop. I stood up and offered her my hand but she declined it as she stood up on her own.

"I'll see you around Elena." I said as I walked away from her leaving her gaping after me.

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**ELENA POV**

I walked into history class and sat down with a sigh.

"What's up Elena?" Alaric asked me leaving his desk to check on me.

"Damon freaking Salvatore." I muttered.

"What's he doing? It may shock you but he's actually brilliant." Alaric said.

"I don't care how brilliant he is. He won't stop asking me out." I muttered running my hands through my hair.

"And that's a bad thing. I hear how girls talk about him and it's always about how they would give anything to go on even one date with him." Alaric said.

"Not me. He's a manwhore. I've walked into the girls bathroom so many times to hear girls crying about how he used them for sex then walked away from them with only a "thank you for a good time."" I said angrily. Every time I thought about him I got angrier and angrier.

"Well maybe he's looking for the girl who could be the one he didn't want to lose." Alaric suggested.

"There is no girl that's more important to Damon Salvatore than himself. That's all he cares about. Himself." I muttered.

"Well maybe Damon needs someone to show him the right way." Alaric suggested.

"No what Damon Salvatore needs is someone to put him in his place. Treat him the way he treats all those other girls." I said.

"Maybe he does." Alaric shrugged.

"Maybe he does." I said as an idea formulated in my mind. But I couldn't do anything about it until I ran it by Caroline. Caroline was good at these sorts of things and she would be able to tell me if the idea is a bad one or not.

"So are you feeling better now?" He asked not aware of what was going through my mind.

"Yep, thanks for the help Ric." I said as I opened my book.

"Elena, I told you to call me Mr. Saltzman while we're in class." He told me but he was smiling.

"Sorry." I said as I pulled some paper out of my binder and waited for the rest of the class to file in.

When Alaric dismissed us at the end of class I walked out to find Damon Salvatore leaning against the wall and I instantly hoped he wasn't waiting for me. I hoped he was waiting for Sophia who was in my class but my hopes were dashed when he joined me at my side when I walked by.

"So what class do you have next? I thought I'd walk you." He told me. Sophia grabbed his arm and forced him to look at her.

"You're seriously doing this to me? You're going after her?" She shrieked and Damon chuckled.

"I'm not doing anything that I'm not allowed to do." He said as he put his arm casually around my shoulder causing me to glower.

"But why her? She's nothing special." She demanded.

"I don't know. I think she's plenty special." Damon shrugged as he turned his back on Sophia. I had to admit I enjoyed watching her get put in her place. She always had herself on such a high pedestal that she really didn't deserve to be on.

"Why are you doing this?" I demanded as I shrugged his arm off of my shoulder. His arm dropped to his side and he chuckled.

"I like you Elena." He said and I knew logically that he was lying. He always did things like this so he could get into a girls pants. It was the only reason he was even remotely tolerable sometimes. He was so good at pretending to be a nice guy when in reality he was horrible.

"But I don't like you." I said in a pleading tone.

"What class do you have Elena?" He asked again.

"Biology?" I answered knowing he wasn't going to leave me alone. While we walked we passed by a forlorn looking Stefan. I wondered what his problem was, he was glaring at his brother.

"Sorry about that. My brother seems to be offended that I'm with such a beautiful girl." He said laying it on thick.

"Well that is one good thing to come from this little walk together. I think he likes me and I don't' like him that way." I admitted not sure why I was telling his brother that.

"Well that's going to break his wee little heart for sure. He's infatuated with you. He talked about it all morning actually." He told me and I groaned.

"I don't want to hurt him, it's just that I don't feel any connection with him at all." I said trying to ignore the spark that crackled between Damon and I.

"I didn't think you would." He said as we walked. I rolled my eyes and sighed happily when we stopped in front of my classroom.

"Here you are." He said and I nodded and fled into the classroom.

When lunch finally came around I left my classroom and met Caroline at your table with my lunch.

"Hey." She greeted me and I smiled at her.

"Whats up?" I asked her.

"Not too much. So how's the Damon Salvatore thing going for you?" She asked me. I rolled my eyes and Caroline laughed. Since he dropped me off at Biology he had walked me to all my other classes and he always tried to carry my books for me. It was hugely annoying and I wished he would stop.

"That good huh?" She laughed. I rolled my eyes again and shook my head.

"He walked me to all of my classes and he asked me out each time. He knocked me over and helped me pick up my books this morning when the first bell rang and he asked me out then. He's trying to wear me down and I'm getting annoyed. But, I have a plan now. It's partially thanks to Alaric." I said and Caroline perked up.

"That's so cute that he's being so attentive. It's so not Damon Salvatore. Do you think he actually likes you?" Caroline wondered aloud.

"No, he's just doing it to get me into bed. I know that. But like I said, I have a plan."I told her.

"And what is that? Oh by the way has Stefan tried to talk to you again?" Caroline asked.

"No, but he didn't look happy when I walked by with Damon this morning. He looked quite upset. But if it persuades him that I don't like him that way, then I guess it's a good thing." I shrugged.

"Yeah, so what's your plan?" She asked me and I smiled slightly.

"I think Damon needs someone to put him in his place. He needs to get denied and dumped not the other way around. I've turned him down a few times but he's never going to get the hint. He's never going to give up, he said as much." I explained.

"So what are you going to do?" Caroline asked.

"I'm going to let him take me out. But he's not going to sleep with me and I'm going to be the one to dump him." I told her.

"So does that mean you're going to have to go on more than one date with him?" Caroline asked.

"Ideally. Which means I have to make it an amazing first date without sleeping with him. It's going to be hard since I know that's the only reason he's here. But I think if I can pull it off, it'll work perfectly." I told her.

"It's a good plan." Caroline agreed.

"But he'll suspect something if I just say yes to him. So I've got to let him continue to attempt to woo me. I'll say yes tomorrow after school because I have no doubt that he'll have more ideas on his mind by then." I told her.

"That's a decent idea Elena. You have to share all the details about the date. I need to know what dating an asshole is like." Caroline said as Tyler walked over and kissed her cheek.

"Hey." She greeted him turning her head and kissing his lips once.

"I'll make sure I tell you everything. He's not going to know what hit him." I said with a grin as I grew more excited about my plan. I told myself I wasn't excited about going on a date with him, I was excited about saving all the girls in this school from Damon Salvatore.

"Let the games begin Salvatore." I grinned as I looked over my shoulder at where he was sitting with his friends.


	3. She Said Yes!

**Damon POV**

Okay, here we go. Day two of seven in the "Make Elena Gilbert go on a date with me so I can sleep with her" plan. This was so not going according to plan, I was supposed to have already won this bet. But no, Elena was being stubborn and I had to admit I kinda liked it a little bit. It was something I hadn't really experienced before. Not that I enjoyed being turned down time after time after time. Today I was going to have to bring my A-game. I was actually running out of time and this was not going as well as it was supposed to. I artfully messed up my hair before walking out of my private bathroom and out of my room shutting the door behind me. The general rule in my family was that if the bedroom door is closed no one will enter. Unless my mother is home, then she just barges into my room whenever she feels like it. She feels like she has some sort of strange claim on me since I am her first born and admittedly the only child she likes or ever wanted. It sucks for Stefan and for that reason alone I feel bad for him. Everything else he brings on himself. When I got downstairs he was sitting at the table and I could see the explosion brewing behind his green eyes. I knew he was going to yell at me and honstly I've looked forward to it since yesterday since he saw me walking down the hallway with Elena.

"What the hell are you thinking Damon? She's mine. She was this close to liking me and then you swoop in and she wants nothing to do with me. What the hell is wrong with you Damon? Do you feel the need to sabotage everything I want?" Stefan yelled and I chuckled. It was better than I imagined. Did I feel bad that I was stealing the girl that Stefan wanted? Yes and no. I felt bad that I was going after a girl he wanted, but since it was Elena all bets were off. She was far too good for Stefan and he needed to learn to go after girls that were in his league. I was more the willing to teach him that lesson. Elena was in my league, she was leaps and bounds better than what Stefan should be able to get.

"Whoa calm down Steffie. Just think of it this way, I'm doing you a favour." I told him and that just seemed to piss him off more.

"You're doing me a favour? How the fuck do you even see that? I know you're selfish and all but I don't get how you can even see the logic in that one." Stefan yelled just as Giuseppe came down the stairs.  
"What the hell are you yelling about Stefan?" He demanded as he carried his brief case. Clearly he was working again today, he was just leaving later than usual.

"Damon is interfereing in stuff that doesn't concern him." Stefan shouted.

"Stop shouting. What is Damon doing exactly?" Daddy dearest asked. In his defense we were both always innocent until proven guilty. He wouldnt' take Stef's side until he knew exactly what I did. I still maintain I was doing him a favour.

"He's stealing the girl I like!" He said raking his hands through his overdone hair.

"And I say I'm doing him a favour." I interjected.

"Why do you say your brother is stealing her from you?" Giuseppe asked.

"I claimed her. I wanted her and now he's just stepping in and wooing her completely." Stefan muttered.

"Wooing her? Really Stef?" I asked.

"Yes. Why can't you pick from the bevy of other girls that are always flocking her every move?" Stefan asked.

"They're boring. I want a girl who can keep up with me. Which she can. She's witty and smart. But most of all, she's a virgin. I want to pop that cherry." I said with a smirk on my face.

"You're stealing the girl that your brother likes because you want to take her virginity?" Giuseppe asked with what clearly sounded like disppointment in his voice. That was fine, it wasn't the first time he'd been disappointed in me and it probably wouldn't be the last.

"Essentially yes. But the thing is, I'm doing Stefan a favour." I repeated.

"Why do you say that?" Giuseppe asked.

"She's not into him. I heard her say it plain and simple. She told me that she felt no connection with him. I'm simply saving him from her having to tell him that to his face." I said feigning concern for my little brother.

"Did she really say that Damon, or are you simply saying that to make yourself look better?" Giuseppe asked.

"It doesn't matter what I say to make myself look better. I'm never good enough in the eyes of this family. Either way I'm going to go on a date with her. I have twenty bucks riding on that." I said as I grabbed the keys to my Camaro along with my backpack and left the house.

When I got to school I walked over to Elena and took the empty seats next to her. None of her friends had arrived yet and as predicted she sighed when I sat down.

"If you're going to ask me out again, you may as well get it over with." She said staring at me.

"Fine, I will. Go on a date with me." I said aware it wasn't my best work.

"Nah. I think I'll pass." She said and I smirked at her.

"Isn't playing hard to get getting a little boring. Imagine how much more fun you'd have if you just said yes." I asked her and she actually laughed.

"But where would the fun being in that? I actually enjoy turning you down multiple times a day." She said to me and I grinned. Oh yes, this girl was definitely one I could keep around even longer than Sophia.

"Guaranteed I'll break down your resistance soon enough." I told her and she smiled up at me.

"Good luck with that." She said and I stood up to join my buddies on the other side of the quad.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Elena POV**

I smiled ahead of me when he walked away. The start of my evil master plan was starting today and I couldn't wait to be the first girl to dump Damon Salvatore. It would put him in his place and hopefully then he would make an effort to get himself into a relationship that was real. He didn't need to only have sex with various girl for his entire life. Everyone needed to have a realtionship. I truly believed that.

"Elena, can we talk?" Stefan Salvatore called to me as he took the seat across from me. I was instantly praying that Caroline and Bonnie would show up soon so I could avoid this awkward conversation.

"Hi, Stefan. Did you finish your English homework?" I asked him making polite conversation.

"Yeah. It was fairly easy. So I just wanted to talk to you about something." He pointed out as he ran his hands through his hair. I recognized it as a nervous habit.

"Sure, what's on your mind?" I asked even though I knew what was on his mind. I also didn't want to talk about it, but I knew that if I didn't he would just keep talking about it.

"My brother Damon. Don't go out with him." He told me and I tried to stop myself from rolling my eyes.

"It's not your choice who I go out with." I told him crossing my arms.

"Elena, he's not a good guy. He'll wreck you like he wrecks everyone else." He told her worry filling his eyes.

"Then that will be my problem not yours. It's my choice who I go out with and it's my choice what I do with them." I told him desperately needing to get my point across.

"I'm just looking out for you Elena." He told me.

"I don't need you to look out for me. I have enough people who do that already." I said to him and he sighed.

"But none of those people know my brother as well as I do. None of them know his intentions with you." He said and this time I did roll my eyes.

"So you don't think I know what I'm getting myself into? Well I do. I've seen how he treats other girls but I also feel like it can't hurt to go on a date with him. He's very persistent." I said.  
"Then go on a date with me. I could date you better than he could since I'm actually intersted in you for more than just sex.' He said laying all of his cards on the table.

"Stefan, I can't. I don't like you in that way." I said to him. I never wanted to hurt him but it seems like I had to anyway.

"That's what Damon said you said. I didn't believe him since he does nothig but lie. Just don't date him please. It'll end badly." Stefan urged.

"I can handle myself Stefan thank you very much." I said when I saw Caroline and Tyler approaching.

"Alright, I'll leave you alone for now." Stefan said and I nodded my head. I knew it wasn't over for Stefan and knew he would keep trying.

"What was that all about? You looked tense?" Caroline asked.  
"Stefan asked me out. I'm not into him in that way." I told her and she nodded her head.

"Ah yes. So how's it going with the sexier brother?" She asked me and I smiled.

"I'll say yes to him today after school. He tried again this morning." I told her as I closed the novel I was reading.  
"That's good. At least he seems to be into you. That's never a bad thing." Caroline shrugged as she snuggled in closer to Tyler.

"It's not. But I just wish someone I could actually like was into me. Not someone that I can't stand." I sighed as the bell finally rang and I headed to class.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

At lunch time there was a bouquet of daisy's sitting on the floor by my locker when I came to drop my books off. I sighed and read the card.

_Go on a date with me. Xoxo Damon._

I laughed and opened my locker stuffing the flowers inside. They were beautiful, how did he know that I preferred wildflowers over anything else. I was not a rose girl, I was definitely a daisy and wildflower girl. I just didn't know how he figured that out. We'd never talked about anything like it. Maybe he was more perceptive than I gave him credit for. When I walked outside I passed by him as I walked to my table.

"Did you get my flowers?" He asked as I walked by.

"Yes." I told him.  
"Do you have an answer?" He asked grinning.

"No." I told him.

"Is that a no?" He asked.  
"Yep." I told him smiling widely now. I loved tormenting him but it was going to feel really good to break up with him.

"I'll get you to say yes soon enough Elena." He said as he walked to his table. I watched him walk away before going to sit with my friends. When I sat down I looked up to see Caroline and Bonnie staring at me.  
"What?" I asked.  
"Are you going to tell us what happened over there with Damon?" Bonnie asked.

"Yeah. This time he gave me flowers. He bought me daisies. I couldn't believe he knew I liked them. But I know he still is the enemy, he's just doing a really good job right now." I told them.

"He's playing a tough game. He's pretty good." Caroline approved.

"I know. But he is Damon Salvatore, so for women everywhere I have to do this." I said nodding my head firmly.

"Have you ever given the idea of you actually starting to like him, or even love him a thought?" Matt asked cautiously.

"It's not possible." I said.

"What if something changes in him while you're fake dating him and he gets better. What if you fall for him?" Matt asked.

"It won't happen so the point is moot." I told him shrugging.

"I'm just warning you. I've seen it happen before. It could happen to you too." Matt told me and I nodded myself.

"I've protected my heart really well from guys like him. I'll be fine." I promised.  
"Okay, as long as you're sure." Matt said nodding his head. That was the good tihng about Matt, is he would take my word for it even if he was certain I was wrong. So I wasn't sure whether he trusted me or not. I couldn't worry about that. I needed to worry about making sure my plan went off without a hitch.

"But if your plan is to be able to dump Damon Salvatore, then won't you have to sleep with him to make him stay for more than one date?" Bonnie asked after pondering for a few minutes.

"I hope not. I hope I can put on a good enough date that he won't want me to sleep with him." I told her and Bonnie nodded her head satisfied that I'd thought of it.

When the end of the day finally came I walked out of the school and towards the parking lot where my mom was supposed to be picking me up.

"Elena, wait up!" Damon called behind me and I stopped happy that he was coming after me.

"Hey, what do you want now?" I asked him.

"You had to have known I wasn't ready to give up. I'm going to ask you again. Will you go on a date with me?" He asked me.

"You really are persistent aren't you?" I asked him and he nodded his head with a grin on his face.

"I am very persistant. If you don't say yes now I will keep asking." He warned me.

"Fine then. Since I want you to leave me alone, I'll agree to one date." I told him.

"Great. I'll pick you up Friday at seven." He told me.

"Fine. Do you know where I live?" I asked.

"Yes. Don't ask how I know, I just know where everyone lives." He told me.

"Fine. I will see you Friday." I told him.

"You sure will. After this date you'll be begging for another one sooner than you think." Damon told me and I grinned.

"We will see about that." I told him.

"You have no idea what you're getting yourself into. It'll be more fun than you've ever had in your entire life." He said cockily.

"I guess we'll find out won't we." I said before walking away from him. He watched me walk away and I grinned. Step one... complete.


	4. The First Date

**Here we go another update. Thank you to everyone who said I should write this. It has been a blast. Enjoy the first date. ;)**

* * *

**Elena POV**

"Ugh, Care you're supposed to be helping me find something to wear." I shrieked as I looked at the clock on my phone and saw that it was 6:30 already. Where had the time gone? Damon was scheduled to pick me up in around a half an hour and I was nowhere near ready. Caroline had invited herself over to help me get ready for my date but so far she was just sitting there watching me with a coy smile on her face.

"I will, I'm just too busy watching you." Caroline said peering at me closer than before.

"Why would you be watching me? You've seen me get ready for dates before." I shrugged unsure of what she was trying to do. Sometimes Caroline's plans or motives really confused me. But admittedly, they always got the job done.

"Number one, you keep calling this a date. Before you finally said yes to him you were calling it a game. Number 2, you're putting an awful lot of attention on making sure you look good, which is odd because it's just a game. You're reminding me

of the first time you went out with Matt. You're just as obsessive." She said knowingly and I shook my head.

"I do not like Damon Salvatore." I said but Caroline laughed and gestured to the daisy's the I still had sitting on my night stand. I had intended on throwing them out when I got home that night, but it never happened. I even caught myself smelling them from time to time.

"I think you do. I don't think you'll be able to go through with it. I think that you think it's a real date." Caroline said in a sing-song voice. Sometimes my best freind really irritated me.

"I do not. Besides it's not real for him. He's just looking to sleep with me. Which by the way is not going to happen. I take great pride in my virginity." I told her still trying to ignore the certain look on her face telling me that she was certain I was lying.

"I know you do. But I also think you're not as invested as you were into breaking him. I think somehow he got to you and

you're wishing me morphs into a good guy sometime before your date." Caroline said knowingly.

"Look, there is nothing between Damon and I. Nothing at all. He doesn't like me that way. He only wants sex from me and I understand that but that doesn't mean he's going to get it. I have a mission tonight and I have to see it through. Now help me get ready or leave, because I don't have time to listen to you psychoanalyze me." I told my friend irritated that she was beginning to see through the facade I had up. I knew there was more going on, I knew that I was developing unwanted feelings for him but that didn't mean I was ready to admit it. Feelings for Damon Salvatore just led you to getting your heart broken. It was the way things were even if I didn't want them to be that way.

"Fine. Wear this." Caroline said getting off of my bed and walking into my closet. She reappeared seconds later with a blue dress.

"Can't. It's casual, we're going to the Grill." I told her shaking my head. I loved the dress but I didn't want to be over-dressed. When he called earlier in the day I asked him what I should wear and he said go casual. Somehow that made me happy. He literally told me that I would look good in anything.

"What kind of date is that?" Caroline scoffed.

"I seem to remember that whenever you and Tyler go out, it's to the Grill." I noted.

"Well with him it's romantic. And because it's hard to get a table anywhere else. Mikealson's has a month long waiting list." Caroline said sitting back down on the bed as I walked into my closet.

"Well he should put his name down and get you guys on that list. It would be romantic. I've heard Mikealson's has the best

food in Mystic Falls." I told her.

"I know and I keep suggesting it but he never goes for it. He doesn't like going out for dinners like that even though I need some romance. Every time we go to the Grill, his friends show up and then it's like a group thing. We never get any quality time together to talk like we used to." Caroline sighed and I came out with a pair of jeans and a lacy shirt that I wore a camisole underneath.

"How about this?" I asked knowing Caroline didn't like talking about her issues with Tyler. It was time to change the subject before she got upset.

"For a casual date that's fine." Caroline shrugged and I went into my bathroom to change quickly. "But you have to wear your sexiest shoes."

"Alright, I have my black ones with the four inch heel that I rarely wear." I called back.

"Perfect." Caroline called happily. She called those my stripper heels. I never really wore them, I never had any reason to do so. Matt didn't care what kind of shoes I wore and they were too painful to wear to school. When I was finished I walked into my bedroom again and looked at my phone. 6:55. Five more minutes to go.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Damon POV**

I pulled up in front of the Gilbert house at exactly 7. It was important when trying to get into someone's pants to be on time. I have to be on my best behaviour or else I will lose this bet and that's not really an option. I have to win. It's not even the twenty bucks I bet for it, it's the idea of losing to Mason of all people. Damon Salvatore never loses to Mason Lockwood. Ever. At 7:02 Elena opened the front door of her house and walked outside. I appraised her look, she was wearing dark skinny jeans that showed off her curves, a black shirt and a pair of insanely sexy heels. I could never understand why girls felt the need to torture their feet with shoes like that, but I definitely liked the effect. I reached over and opened her door for her and she got in.

"Thank you." She said as she buckled her seat belt.

"You look amazing." I said and he found himself meaning it. To me girls always looked hot, of sexy but amazing was a

word I rarely used.

"Thank you." She said as she stared straight ahead.

"You ready?" I asked as he put the car into gear.

"Yep. Let's go." She said and I started driving.

When we got to the Grill, I took a deep breath and got prepared to play the game of my life.

"You know you look incredible right? By far the hottest girl here tonight." I said to her and she didn't respond.

"Should I say thank you?" She asked.

"It's true. God, every guy in here tonight wants to be in my place." I said aware I was laying it on thick. But sometimes it worked to smother the girls in compliments before I start going for the win. I needed to make her comfortable. She was on edge like she didn't know what to expect from being out there with me. When the waiter showed up, who I recognized as Matt "the wonder-jock" Donovan, I told Elena to pick whatever she wants.

"Elena, how are you doing tonight?" Matt asked MY date. He was completely ignoring me but he was talking to MY date, what kind of bullshit game was he trying to play.

"I'm fine." She answered with a smile on her face.

"So how's the big date going?" He asked her. She smiled at him and nodded her head.

"It's fine. It really just started." She answered and Donovan nodded.

"That's good, so what can I get you?" He asked, I knew logically he was asking both of us, but the question was pointed towards her.

"I'll just have a coke and chicken fingers." She told him without even looking at her menu. It was clear how much time she spent in this place. The place wasn't bad, but she needed to get more of a life apparently.

"I'll have the burger and a coke. Now run along Jock." I said with a wave of my hand and Elena glared at me.

"What the hell is your problem?" She demanded and suddenly this evening was not going as I had planned it.

"We are on a date, therefore I want to be alone with you." I said apologetically.

"He is one of my closest friends and if I want to talk to him I will." She told me firmly. Her arms were crossed on her chest and she was glaring at me, clearly challenging me to argue with her. I quickly shook my head needing to get the mood I was trying to set for the date back on track. At this rate I was never going to sleep with her. We fell into silence and she looked disappointed, almost like she wanted me to fight with her about it. I didn't understand it and I knew despite my own wishes I was going to ask her.

"You wanted me to fight with you didn't you?" I asked her and she stared at me for a minute before clearing her throat.

"At least it would have been real." Was all she said.

"What are you talking about?" I demanded not sure what she was talking about.

"This, is all a game to you. I know your motives for going out with me. I'm not stupid Damon, at least you not constantly trying to impress me was normal." She explained and my jaw literally dropped.

"If you know why I'm here then why are you here?" I finally asked.

"Because I have the usual teenage girl issue of hoping she's wrong about someone. I just have one question for you." She told me and I swallowed thickly. This was definitely not going the way I had planned it, there was no way I was getting laid tonight now.

"Shoot." I told her knowing it couldn't get any worse now.

"Why do you act like this? I'm sure deep down inside there is a decent person, but this you is anything but." She asked me and I wasn't expecting the question. There were a million different questions that she could have asked but she went for that one instead. No one had ever blatantly asked me that before and I was in shock.

"Because it's safe." I answered knowing it was the truth in so many ways.

"Maybe for you but what about all the people you hurt in the process?" She asked. Her questions were digging into my soul and I had no idea when or why I decided to actually answer them.

"I've never worried about them. I have commitment issues and that's the basis of everything." I told her honestly and she

just stared at me.

"I could have told you that you have commitment issues. Why do you feel that way?" She asked. She wanted to know everything, her beautiful brown eyes were alight with curiosity.

"You're not my shrink Elena."I bit back.

"I know I'm not. I'm just curious about what makes a man do what you do. Why aren't you willing to let yourself possibly fall for someone. Isn't it better than just using people for your entire life?" She asked and I sighed.

"I've never seen a functional relationship so I've never wanted one. Marriage and commitment has always brought bad shit into my life." I told her.

"What do you mean? My parents have been together forever. They met at college and got married. They're still happy

together." She told me and I shook my head.

"Not everyone is as lucky as you are Elena. My mom and dad are still married but it's only on paper. My mom spends most of her time in Italy, gathering Italian painters while my dad stays home and raises Stefan and I." I told her.

"I hope you mean gathers Italian paintings." She said.

"Nope. She likes painters. The younger the better. They're the only type of guy she sleeps with. She wants me to join the family business, but I have no intentions of doing so." I told her.

"She needs a male Salvatore in Italy with her to seduce all the female artists to?" She asked knowingly.

"Yep, that's exactly it. I don't want any part of it. She has made commitment seem really bad to me over the years." I admitted.

"At least it makes sense now. But it doesn't change anything, I'm not going to be sleeping with you tonight." She told me and I had to smile a little bit. I was in immediate danger of falling for this girl. She was feisty and beautiful. She had a body to kill for and she seemed to genuinely care about my past. This definitely wasn't the way I had planned for tonight to go. Not at all. Not even a little bit. Nuh-uh.

"Hey, if it means anything I'm sorry for asking you out with that intention." I decided to apologize, because yep my balls were officially in the palm of her hand. I would do whatever she asked of me. I never used to be one of those "love at first

sight" guys but here it was. I had to regain control of the situation somehow. I just didn't know how.

"It's okay, because I'm not entirely innocent either." She said and I perked up.

"What did you do?" I asked her.

"I accepted your date so I could be the girl to finally dump you. I just wasn't too sure how to get more than one date with you." She admitted with an apologetic look on her face.

"So that's why you finally gave in? I was beginning to think that I was never going to get a date with you." I laughed as Matt returned with our meals.

"Yeah, I'm not proud of it. But there is it. So you really don't need to apologize for your intentions. I didn't have good ones either." She told me. She tore some of a chicken finger off and dipped it into the sauce before taking a bite as we lapsed into silence for a moment. I wasn't sure what to say to that mainly because I didn't want to piss her off. Suddenly losing twenty bucks to Mason didn't seem so bad.

"So now that we both know each others motives, where do we go from here?" I finally asked.

"I don't know." She admitted.

We finished our dinner and grabbed our jackets. It was the end of that and the date was over. After our revelations there was nowhere else for us to go. I wish I could think of something to persuade her to go out with me again, but I've never done that before. I don't know how to actually ask a girl out.

"Are you ready to go home?" I asked her and she nodded her head. I paid the bill and we walked out of the Grill heading back to my precious Camaro. We made the drive back to her house in silence and she smiled before she got out of the car. Once she was unlocking her door I drove away, cursing myself for being such a pussy.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Elena POV**

Monday morning came around and I hadn't heard from Damon, not that I expected him to. But it really felt like we had a connection and it bothered me that he clearly didn't feel the same way. I got ready for school the same way I usually did and waited for Jeremy downstairs so our dad could drive us to school. Caroline had been texting me since Friday night, asking me how it went but I dodged her question over and over again. It was lucky that Tyler had kept her occupied all weekend so she couldn't interrogate me in person. I didn't know what to tell her.

"Ready to go?" My dad asked and I nodded. Jeremy came racing down the stairs a moment later with his backpack on.

"We both are." I said and the three of us left the house.

When we got to school I walked to our table where Caroline was sitting with our other cheer leading friends.

"Hey, where have you been all weekend?" Caroline demanded when I sat down.

"Busy." I answered.

"So how did it go with Damon?" She asked me all business now.

"You and Damon Salvatore?" Chloe asked and I nodded. Chloe was a really good friend. She was a senior and a cheerleader with Elena and Caroline. She had given the captain spot to Caroline since she was only there for fun. Caroline

was intense enough about the job to do it well.

"Sort of. The date didn't go anything like I thought it would. I'm not sure where we stand right now." I admitted leaving

Chloe confused and Caroline with a knowing smirk on her face.

"So your little plan didn't work did it? You do like him." Caroline shrieked.

"I think you're right, but he's not into me." I said as I watched him walk onto the quad and sit down next to his friends.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Damon POV**

When I sat down I slapped down a twenty dollar bill and Mason whooped in response.

"You got shut down." He cheered and I shrugged.

"Whatever. Doesn't really matter." I said. I finally had a plan for my Elena situation and I was going to take care of it this afternoon.

"You were all gung ho about taking her virginity. What happened?" Mason asked stuffing the bill into his wallet.

"Not much." I said shrugging again.

"So is it cool if I go after her then?" Mason asked and I knew I had to tread this potential mine-field carefully.

"Do whatever you want, but guaranteed she'll say no to you." I said.

"I'm not going to ask her now. I have a couple other people on my radar right now." He shrugged and I matched his expression.

"Whatever suits you." I said. When the bell rang I got up and walked away from the table intent on putting my plan into motion as soon as possible. I would feel so much better if I just got it over with now. I stood around the corner from her locker as she walked by. When she did I grabbed her arm and pulled her into the conveniently located supply closet.

"Damon, what the hell?" She demanded as her eyes adjusted to the darkness.

"I needed to talk to you. It's important." I told her and she put her hands on her hips and stared at me.

"Well..." She trailed off indicating that I should start speaking.

"Okay, well..." I started unsure of how to do this. I decided instead of speaking I should just act on impulse. That usually worked well for me. I leaned down and kissed her. She actually kissed me back for a moment before she pushed me away.

"What was that?" She demanded.

"That was me wanting to do that over and over again." I told her unsure if she caught my drift or not.

"What are you talking about? I can't spend all class in here making out with you." She said raking her hands through her hair.

"Not entirely what I meant." I said dryly, but my nerves were crazy. It was the first time in a long time that I actually felt nervous about something. It was unheard of. Especially around a girl.

"So you want to date me?" She asked and I wasn't sure how she got that from what I said. But it was closer. Significantly closer than before.

"Sort of. First just tell me if you would ever be interested in going out with me?" I asked her.

"Yeah. I was quite pissed when you didn't want to give it another shot last weekend." She told me and I sighed in relief.

"Well okay. But dating is really not an option for me. I'm not that guy but I want to be with you." I told her and she laced her fingers through mine and I looked down at our hands.

"Then what can you do? I know what you've been through and I understand you're scared of being in a relationship. But I like you Damon. I don't know why, because there is nearly absolutely nothing good about you. But I like you, so you tell me what you're able to do." She told me and I was shocked. I had to chuckle a little bit at her ability to insert an insult into a perfect compliment.

"I don't want anyone to know. I need to be able to keep this a secret for a while. Just until I figure this out." He told me and she was silent for a while.

"So you just don't want to be public. What does that entail?" She asked.

"It's not ideal, I know. But just that we don't go anywhere people can see us." I told her and she nodded her head.

"It's not ideal. But like I said I like you and I'm not in the business of denying myself anything that I want. I'm willing to try it." She decided and I grinned. I bent my head and kissed her again, my tongue teasing the seam of her lips. She pulled back not willing to deepen the kiss yet.

"I have to go." She said. We both heard the second bell ring so I nodded her head.

"I'll see you later." I said as she walked away. I gave her a minute to get away before I left the supply closet and headed to my own class. I had no idea what I was doing but I loved every second of it. I was dating, Elena Gilbert for all intents and purposes, never would have saw that one coming.


	5. Just a Friend

**Okay, here it is. if you think this moves a little too fast, it's just because it's not meant to be a crazy long story. Somewhere between 10-15 chapters and I don't know about you but I like to get the unhappy parts over a lot quicker than the happy parts. Enjoy this longer chapter and let me know what you think. Tell me what you like about the chapter and what you don't. Also if any of you have any suggestions for the baby's name in ETU then pass them on too. It's a little girl for those who haven't read the update yet. I forgot to ask in the non-existent authors note on that chapter. Thanks for reading and reviews and ENJOY.**

* * *

Damon Salvatore and I had been seeing each other for two weeks by now and it wasn't ideal but I was having fun. No one knew about us and the sneaking around was pretty sexy. We had made out in his car for a little while every day since we started seeing each other. When the both of us were at the Grill at the same time we would subtly go outside and make out. The make out sessions were good and I loved them but I wasn't ready to take that next step yet. I was nowhere near ready to give up my virginity for a guy who may or may not be my boyfriend. I carried my tray across the quad when he intercepted me and pulled me aside where no one could see us. We were against the side of the school away from the prying eyes.

"Come to the Falls tonight." He told me when I was pressed against the side of the school.

"Why?" I asked him.

"There is a party, I'll be there, so you should come and hang out." He told me.

"But we're not going to be together." I reminded him. My hands rested on his sides and I loved the freedom I had in touching him as long as no one else was around. It was definitely lacking several ideal factors but it was something at least.

"We'll steal some time." He told me and I sighed. I didn't want to tell him but I was honestly getting tired of hiding

everything from everyone. I've been lying to everyone I know for the past two weeks and it was starting to bother me. I was holding out hope that he would decide he wants to be public and exclusive soon enough.

"I don't have a way to get there and you can't come get me." I told him.

"Just give it a shot please. For me? I really want to see you tonight." He insisted leaning down and pressing a single, solitary kiss to me neck.

"I'll see what I can do." I sighed.

"Good, I think Chloe is coming. Ask her to drive you." He suggested and I nodded my head.

"Alright. I'll ask her." I told him and he kissed me on the lips, shoving his tongue between my lips. He had the presence of mind to hold my lunch tray while he kissed me, knowing that I tended to forget everything when his lips were on mine.

"I'll see you tonight." He said before walking away from me. I paused to catch my breath before walking out to join our friends.

"What happened to you? You were right behind me in the lunch line." Caroline demanded when I finally sat down after my dalliance with Damon beside the school.

"I got caught talking to a friend of mine." I told her not really lying.

"Which friend? I thought I was friends with all of your friends?" She asked suspiciously.

"Just a friend." I told her not willing to break the promise I made to him. If I wanted him to trust me enough to be public with me, I couldn't blab about us to anyone.

"You've been spending a lot of time with a friend lately." Caroline noted.

"I'm allowed to hang out with other people than you." I told her shaking my head. If I wasn't careful, all of Caroline's questions and jabs were going to get to me.

"So are either of you going to the party tonight?" Chloe asked, somehow having the instinct to rescue me from Caroline.

"Nope. Neither of us are going. I have plans with Tyler and Elena never goes to these things." Caroline answered for the both of them.

"Actually maybe I'll go with you tonight." I decided.

"Cool." Chloe said grinning at her.

"You're actually going to a party?" Caroline asked dubiously.

"Yeah, why not?" I said grinning. I had her way to the party, so now it gave me more time to make out with my sexy semi-boyfriend.

"You've never had any interest in going to a party at the Falls before." Caroline pointed out.

"Well maybe I want to get out tonight." I shrugged.

"You've been weird for the past little while Elena. What's up with you?" Caroline asked me.

"Nothing. I just don't want to sit at home tonight." I shrugged, trying to brush everything off. I didn't want her to start suspecting anything. She stared at me for a minute, as if she was trying to figure out if I was lying or not. She seemed satisfied when she focused on her lunch once again. I breathed a sigh of relief as Chloe looked at me curiously. I shrugged and focused on my salad in front of me.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Damon POV**

I watched her across the quad, I was trying to be subtle about it, it was important that I was. I didn't want anyone else knowing that I was majorly crushed out on Elena Gilbert.

"Yo, Salvatore, you coming to the party tonight?" Mason called, commanding my attention for a moment.

"Yeah, I'll be there." I told him as if he was stupid for even asking. Did I ever miss a party? No, I certainly did now.

"Hello, Damon." Heather, one of the many girls I've slept with said as she walked by. I smirked at her but mostly just ignored her. I had a rep to keep up. I wasn't in a public relationship and I needed to make sure everyone knew that. I wasn't sleeping around anymore, but I had to make it seem like I was. I didn't need anyone detecting any change in me.

"So, I was wondering if we'd maybe meet up again sometimes soon?" She asked running her hand down my arm.

"You know I'm a fuck em and leave em kind of guy." I reminded her.

"I know that, but you know it was fun that first time." She urged me. She had moved her hands to my chest and ran them down. I stopped her and put her hands back by her side.

"Fuck em and leave em. I already fucked you so that means we're done." I told her.

"You're such an asshole Damon." She hissed as she walked away. I turned my head and saw Elena's eyes on me, if I didn't know any better I'd swear she had a smirk on her face. She must have liked watching me turn down a girl for sex, not that she'd ever actually admit that. Since I refused to be public with her, she refused to say anything remotely nice to me most of the time. We'd make out and that was about it. She wouldn't sleep with me, but right now I was cool with the kissing. She was absolutely incredible in that department. Her tongue and lips worked wonders on me. I have never been kissed the way she kisses me. I'm pretty sure she could get me to agree to almost anything when we were kissing. But so far she hadn't tried anything.

"So you coming tonight?" I asked Klaus who was seated beside me but staring over at Caroline Forbes. He glowered when he saw Tyler Lockwood lean down to kiss her lips.

"That prick isn't good enough for Caroline." He growled.

"Not what I was talking about Klaus. Are you coming to the party tonight?" I asked him laughing. I vowed that I would never be as pussy-whipped as Klaus was. But I was well on my to being fucked though.

"Yeah I'll be there. As always. My mom is going to be pissed though, she seems to think I should stay home and Skype with Bex and the rest of them." Klaus said.

"So why are you coming?"I asked him. I knew Klaus didn't actually enjoy the parties all that much. He came mostly to keep me busy until it was time for me to find someone to take home with me.

"I don't want to talk to my siblings and because I need to keep any eye out for you and your mystery girl." He told me, his voice quiet so the other guys didn't hear.

"What the fuck are you talking about?" I demanded. It didn't bother me if Klaus knew something because he was my best friend and out of anyone on the planet I knew he wouldn't betray me.

"You know, the girl you've been sneaking around with for the past couple of weeks. Don't think that I didn't notice." Klaus laughed and I shook my head.

"How did you figure it out?" I asked not denying anything.

"It was obvious. You disappear every so often and you come back happier than before. I don't think you're sleeping with her since your brief dalliances with her are very brief. I think you're hooked on a girl." Klaus laughed and I shook my head.

"I can't believe you know that." I laughed.

"Well I do. My amazing detective abilities also know who the mystery girl is." Klaus pointed out.

"Oh you do do you?" I asked laughing. It really didn't bother me knowing that Klaus knew. I would have told him soon enough anyway.

"Yes I sure do." He grinned and clapped me on my shoulder. I knew from his mannerisms that he knew exactly who it was.

"Well good for you. You're sworn to secrecy, do not tell anyone. At all." I warned him and he made a show of crossing his heart.

"Worry not dear friend. I won't tell a soul. What I don't understand is why you don't just come clean. Won't both of you be happier that way?" Klaus asked and I shook my head.

"Man, you of all people know I'm not that kind of guy." I declined.

"Yeah, but I'm sure Elena Gilbert will be the one to tame you." Klaus predicted. I shook my head not even wanting to talk about losing my identity. The simple idea of it scared me to death.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Elena POV**

"So what are your plans for tonight, sweetheart?" My dad asked me when I walked in the front door.

"Actually, Chloe is picking me up to go to a party tonight." I told my dad. Aside from one really big one, I didn't have

secrets from my parents. Damon Salvatore was the sole exception and it was slowly killing me.

"Is Chloe the friend you've been spending lots of time with?" My dad asked me.

"No." I admitted, not willing for there to be another lie between us.

"So who is this friend?" He asked.

"Just a friend." I shrugged. My dad didn't respond, he just shrugged his shoulders and went back to the paper he was reading. That was one thing about my dad, he didn't push me and he believed everything I told him for the most part. I had never done anything to disappoint them, so I had that level of trust that many people I went to school with didn't have.

"Just be home by curfew." My dad called as I started walking upstairs to my bedroom.

"Always." I called back.

At dinner time I came back down with all of my homework done and sat down in my usual seat across from my brother Jeremy. My mom had just walked in the front door and sat down with a sigh.  
"There is so much gossip in this town that I have no interest in." She laughed shortly

"I know." I agreed with her. She had no idea how bad it was in high school. Whatever she was hearing was no worse than what I heard on a daily basis.

"So what went on with you two today?" My mom asked my brother and I.

"I just went to school. Nothing to remarkable happened. I also have no plans tonight." Jeremy answered knowing that would be the next question she asked. Jeremy and I knew exactly how these conversations went.

"How about you Elena?" My mom asked.

"Nothing happened at school today aside from tons of gossip. But that's a usual Friday night. But Chloe and I are going to a party tonight." I told my mom.

"Good for you. No drinking right. I know there is drinking at these things but I don't want you getting involved in that." My mom told me.

"I know. But I should go get ready. Chloe is picking me up early so we can get there early-ish. I have a curfew and I have to say hi to everyone there." Elena said glancing at the clock and seeing that it read 6:50.

"Alright, have fun tonight Elena. You're only young once." My mom told me as I clearly my plate and walked back upstairs. When I was upstairs I locked myself in the bathroom that connected Jeremy's and my rooms. I took a quick shower and quickly blow-dried my hair and did my makeup. I left my hair straight and applied my usual makeup. I wasn't one of those girls who piled on the makeup. My skin was nice and I liked showing it off. I was blessed with my mothers complexion. I was lucky. When I was finished in the bathroom I walked back into my room and pulled a mini skirt out of my closet along with a tank top that I intended on pairing with my leather jacket. Damon loved my leather jacket and I loved driving him crazy.

At 7:30 Chloe honked here horn and I rushed downstairs.

"I'll see you guys later." I called to my parents before leaving the house. I didn't take anything with me, I didn't need anything. Drinks and these places were free and I didn't need ID, even a fake one.

"Hey." I said when I got into the car next to Chloe.

"How's it going?" She asked when the door was shut and I was buckled in.

"It's good." I told her as she pulled away from the curb.

"So I have a question for you. Well it's not really a question, it's an observation." Chloe started.

"Sure." I told her, willing to answer almost anything she had to ask me.

"Okay, so this friend you've been spending a lot of time with, is it a guy?" She asked me and I sighed.

"Fine, I'll admit it. Yes." I told her.

"Are you keeping it a secret? If so why?" She asked.

"We're exclusive I think, but he's not ready for everyone to know about us. He's not really familiar with exclusive relationships. It's just easier this way." I explained.

"I see. Why don't you just tell Caroline that you're seeing a guy." She asked me.

"You know Caroline. You know how she would react to that information. She would want to know everything and she wouldn't stop until she does. It would ruin everything." I told her as we neared the Falls. There were already lots of cars there, even Damon's Camaro was already parked.

"I know Caroline is pretty intense." Chloe laughed.

"She is. I'm hoping someday he wants to tell people about us." I told her and she smiled at me as she found a place to park.

She grabbed a spot that she knew she could get out of easily when it was time for us to go. That was the kind of friend Chloe was. She would grab a spot so we could make a quick getaway so I was home for curfew.

"Is lover boy here tonight?" Chloe asked.

"I think so." I said as we got out of the car. I didn't want to tell her who he was. I didn't want to break my promise.

When we walked up to the keg, Damon was talking with Klaus and Mason and I made every effort not to look at him. I was playing a game that I was getting dangerously good at. I quickly got my beer and walked away, I could feel his eyes on my back. He could get away with staring at me since he pursued me for so long at school. He had his reputation so he could stare but I couldn't. If I started staring at him, people would suspect something is up between us. I was supposed to hate him and he was supposed to want to get in my pants. Which he clearly still wanted.

"Don't look now but Damon is still staring at you." Chloe told me as we walked away.

"I know. He just doesn't give up." I laughed.

"Well I am going to go mingle. I'll catch up with you later, unless you want to come with me." She told me.

"Nah, I'll just hang out around here." I declined. I knew Damon would be coming to find me soon enough and we needed to be covert about it. I didn't have to wait long before he sidled on over to me with two beers in his hand. He could approach me without too many people questioning him, I just had to be careful. This was far easier for him than it was for me. It really wasn't fair.

"I brought you this." He said handing the beer to me. I gave him my empty cup and he tossed it into the garbage can a few feet away from where he was standing.

"Thank you." I said taking a sip of the amber liquid.

"Meet me in the woods in about five minutes. Just follow the path between those trees right there. I need to be alone with you for a few minutes." He told me before walking away. No one would have suspected anything from that conversation. I didn't even smile. When my allotted five minutes were up, I started walking down the path that he pointed out to me. The one that I had just seen him walk down. I walked a little ways into the woods when I felt his arms close around my waist hauling me against his chest. He quickly spun us around so my back was pressed against a tree and his lips were on mine. He devoured my mouth, pushing his tongue past my lips and duelling with it. By now I knew exactly how he liked to be kissed. We had been doing it every day for two weeks now pretty much, so you probably got pretty good at it in that time frame. My hands sat on his sides while he did all the work. His tongue plundered my mouth and he slid his hands down to my ass and squeezed. Damon picked me up and I wrapped my legs around his waist as he ground into me. I could feel his hardness pressing into me and I knew we would need to stop this sooner rather than later or else we wouldn't be and I wasn't ready to go there yet. He slid his hands under my skirt and touched my ass over the fabric of my panties. He groaned into my mouth when he felt the boy-cut panties, I knew he preferred those over anything else.

"You're trying to kill me." He groaned when he finally broke the kiss.

"Not intentionally." I told him.

"Then please, don't make me stop." He insisted as he went to my neck and started sucking.

"I have to. I can't go any further until I know if we have a future." I told him unwrapping my legs from around him.

"Elena, you know I can't go there." He told me annoyed. We've been having this "conversation" almost every day for the

past few days. I didn't know how much longer I could go like this.

"And I can't go like this for much longer." I told him shaking my head and stepping away from him.

"I thought you understood what we were doing." He said crossing his arms.

"I do, and I was cool with it because that meant I got to be with you. But we're not going anywhere." I told him.

"Are you breaking up with me?" He asked.

"No. Not yet. I'm just warning you, I don't know how long I can do this for." I told him. He nodded and stepped further back, indicating that I should start walking back to the party. I was suddenly no longer in the mood to party. I just wanted to go home.

When I came back, Chloe found me and grabbed my arm.

"It's Damon isn't it?" She asked me. I nodded my head and sighed. "Are you alright?"

"I'm fine, but I can't pretend like this for much longer. He has to make a decision and I don't think I'm going to like the decision he's going to make." I murmured.

"Do you want to leave?" She asked me.

"I kinda do." I told her hating to make her leave.

"Do you want to go home or are you willing to go to the Grill with me to have a coke and some fries?" She asked me. I hated myself for tearing her away from the party so I nodded my head. Honestly that felt nice, fries and coke sounded great to me.

By the time Chloe dropped me off I was late for my curfew.

"I'm sorry if you get into trouble because of me. I completely lost track of time." She told me as I got out.

"It'll be fine. I'm just happy you got me out of that party when you did." I said smiling at her.

"Alright, I'll see you Monday." Chloe said and I shut the door heading up the front walk.

"Where have you been? You're almost an hour late for curfew." My dad shouted. He never yelled unless I was late for something. When I was late he started worrying.

"I just lost track of time." I told him.

"Come in here young lady. Your mother and I were talking." He said and I walked in.

"What's up? I'm really tired and I want to go to sleep." I told them.

"We want to know what's going on with you. You've been so secretive over the past couple of weeks. We know all of your friends except for this "just a friend" you've been spending so much time with. You have to tell us what's going on with you." He told me.

"Nothings going on. I promise. Me and my friend aren't going to be spending much time together anymore." I told them sighing. I had to stop lying and this was the last time.

"Are you sure?" My dad asked.

"Yeah." I told them as I walked upstairs. When I finally fell asleep, I slept fitfully.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

The next morning I woke up to Caroline sitting on the chair across from my bed.

"Alright, you and I are going to talk. I feel like you've been hiding things from me for so long and I'm getting sick of it."

Caroline told me and I groaned.

"I've had a really crappy night and I don't want to do this now." I pleaded.

"You have to. Who is this "friend" that you're spending so much time with. It feels like you've replacing me." She told me and I sighed. Caroline always managed to make things about herself. It was a talent really, but she was my best friend for a reason.

"Look it doesn't really matter anymore." I told her.

"And why are you spending so much time with Chloe? You're my best friend not hers." She reminded me.

"Chloe has been a really good friend lately as I deal with my other friend." I told her.

"Chloe knows your other friend doesn't she?" Caroline asked me hurt.

"She does." I admitted.

"I'm your best friend Elena. I hope at some point you remember that." Caroline muttered as she stood up and walked out.

"Shit." I sighed and ran my hands through my hair. It was decided, I was staying in bed for the rest of the weekend. This thing with Damon was making me lose everyone and I couldn't let that happen.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

When Monday morning came around my parents weren't upset with me. I didn't leave once for the rest of the weekend and they saw I was seriously sorry for lying to them. I got up and got ready for school. I had several ignored text messages and a couple missed calls from Damon where he was essentially booty calling me. I didn't answer them and I had no intention of doing so. I would talk to him at school today. When I got downstairs my dad was waiting with his keys in hand. I couldn't wait until I got my license so I could drive myself. My life would be so much easier and less dependant. My dad drove us to school and I got out walking to my table where Chloe and Caroline were sitting.

"How's it going?" Chloe asked me but Caroline ignore me.

"It's going. I'm ending things today." I told her and Chloe looked at me sympathetically while Caroline glared.

"So you guys have a special code too?" She demanded.

"It's not special. There is just no point in telling you since it'll all be over with today." I told her sighing. I didn't need her acting like a baby. I turned my head and saw Damon sit down at his table. He stared at me but I wouldn't look at him. Now was not the time or place to have this conversation.

When I walked to class, Damon intercepted me and pulled me into the same supply closet he asked me out in over two weeks ago.

"Why have you been ignoring my messages?" He demanded.

"Look I have to get to class." I told him.

"Fine, if you won't talk to me now then meet me after school. I'll pick you up down the street and drive you home afterwards." He told me. "

"Fine." I said. I was relieved that he wasn't making me talk to him now, I needed the time to mentally prepare.

But of course luck would have it that the end of the day came quicker than it should have. Quicker than it would have on a normal day.

"My mom is picking me up if you want a ride." Caroline told me as we stood at our beside each other lockers.

"It's okay, I have another ride." I told her smiling at her.

"Do you want to do anything tonight? I'm sorry I snapped at you. I just want us to be friends again." She told me.

"Come over tonight after dinner. I'm going to have lots to tell you one way or another. I have something to deal with right now." I told her.

"You're going to tell me everything that's been going on?" She asked.

"Yeah. I'll tell you everything you want to know. Just so you know Chloe only knows because she figured it out on her own." I told my best friend.

"I just feel so left out." Caroline sighed.

"I know, but I really have to go." I told her. Caroline nodded and walked down the opposite way of the hallway while I walked towards the back doors. I started walking down the sidewalk when Damon pulled up next to me. I opened the door and slipped inside shutting the door behind me as he drove away. He drove until he got to a deserted parking lot a little ways out of town. Of course he would take us somewhere we wouldn't be spotted. That was so Damon.

"So you going to tell me why you've been avoiding me since Friday night?" He asked with his hands on the wheel. He wasn't looking at me, he was staring straight out the windshield so I did the same thing.

"I have a question for you. Do you ever plan on not keeping us a secret?" I asked him and I sighed.

"This again? Elena you know why I can't tell anyone." He told me and I sighed.

"What if I asked you to stop making me keep it a secret?" I asked him and he sighed.

"Elena, if you start telling people then everyone would know and it wouldn't work anymore." He said.

"Well I can't keep it a secret anymore Damon. I'm sick of lying to the people that I love. My parents are worried about me and my friends hate me for lying to them constantly. I can't do it anymore." I told him refusing to let my emotions out. A fake relationship wasn't worth the tears I wanted to cry.

"So you're basically giving me an ultimatum." He clarified.

"Not really. I'm just telling you that I can't do this anymore. I need more and if you can't or won't give me more then we can't do this anymore." I told him.

"I'm sorry Elena." He said and he sounded like he meant it.

"That's what I thought. It's okay. Can you just take me home?" I asked him. He nodded and started up the car again. He drove me home but he stopped down the street, even now not able to have us be seen together. I sighed and got out not stopping to look at him before he drove away.


	6. Mama Mikealson

**Damon POV**

Day 3 after Elena. Man this totally sucks. Just a few days ago I was in my first exclusive relationship, and yes I know it wasn't perfect but it was a huge step for me. But she couldn't stay in a relationship like the one I was offering her, and honestly, I really can't blame her. I was asking so much of her but giving her nothing. I made her keep us a secret, despite how awful I knew it made her feel. She hated it and she had to lie to so many people to keep the facade up, but I didn't care. Well I did care, I just wouldn't do anything about it since I was more worried about how it would affect my life. My reasons were some that I found really hard to explain to Elena. I told her it was because I've never seen a functional relationship before and that's part of it, but the main part is that I don't want her lumped together with all the one night stands that I've had. I was about as public as you can get with them and I don't want them to be in the same category as Elena Gilbert. There is no comparison. They were just sex, and Elena is more. So much more. And no matter what I say, everyone would just put her with them. They would compare her to Sophia and that's far from right. Sophia Reynolds is nothing compared to Elena Gilbert, and that's something I figured out even without sleeping with her. Elena Gilbert is more than a guy like me could ever aspire to have. She is perfection and I blew it with her in some misguided attempt to keep her separate from the bad parts of my life. I'm a god-damn fucking idiot.

"Man come back to Earth. What's going on?" Mason asked me, it was Thursday morning so there was only one more day of school after this before I could stay at home all weekend licking my wounds and missing the girl that's way too good for me.

"Nothing." I told him shrugging. I needed to keep my facade up. I am Damon Salvatore and nothing fazes me. Especially not a girl. The good thing is that the only one who knows it's a girl tying me up in knots it Klaus and he'd never tell anyone.

"Well good because I have a problem that I need you to solve for me." Mason told me and I sighed. Mason's problems were always girl related. He didn't have near the success with the opposite sex as I did. He was good, I'll admit that but for every one girl he's screwed around with, I've fucked three. It's just the way that it is and women just flock to me.

"What's up?" I asked him.

"How the hell did you mange to get Elena Gilbert to go out with you? I have to but the girl is a tough one to crack." He said shaking his head.

"You've been asking Elena out?" I asked him completely shocked. I had hoped his little fascination with my girl would have went away by now. I guess technically she's not my girl but whatever.

"I've been trying to but she slips away from me and hides before I even have a chance to talk to her. Tell me how you got to her so I can take her out and succeed in what you failed to do." He told me.

"Why should I give you my expertise?" I asked carefully.

"Since you're my buddy and we both know she needs to be freed from that pesky virginity." Mason explained and I shook my head.

"Nah, I'm not going to give you the advice to get into her bed. Besides it wouldn't happen anyway. You'll never sleep with her,, she's firmly attached to her virginity." I told my pal trying to hide my actual investment in the issue.

"Come on man. We've got to have each others backs." He insisted.

"Nope, I didn't have any help so you don't get any either." I said and Klaus stared at me with a smirk on his face. He knew exactly why I wasn't willing to help.

"Mikealson, how did he do it? You know everything about him pretty well." Mason demanded.

"Can't help you. I don't think this is a good idea." Klaus told him. Klaus always had my back and he knew without me even saying it that I wanted her back. I just didn't want the rest of the damn school lumping her together with all of my other conquests. For the first time ever I really regretted behaving like I do. If I hadn't slept with all those girls, I would have been able to go public with her without any problems at all. Yep, I'm an idiot. They say that hindsight is twenty/twenty, and it's true. I never would have played the manwhore if I'd known that I would meet Elena Gilbert and fall for her.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Elena POV**

"I still can't wrap my head around the fact that you were essentially dating Damon Salvatore." Caroline told me when she sat down firmly attached to Tyler's side.

"It doesn't matter now. He couldn't give me what I need so I can't give him what he wanted either. I know he didn't want to

break up, but he let me go because he knew I didn't have a choice. I couldn't continue lying to everyone." I told her.

"You really liked him didn't you?" She asked. That was the one question she never asked, so I figured it was safe. I didn't have to admit that I cared for him in a way I've never cared about someone before. I missed him, and it was likely that if he asked me and told me he wouldn't hide anymore I would go back to him in a second. There was no doubt about it in my mind. He was so different the times we were together. We talked and he told me things. It was nice having that connection with him, but I should have known then that we had no future.

"I did. I think if everything would have gone the way that it was supposed to, I could have fallen in love for the first time ever." I admitted. I was really trying to total and complete honesty with her. She deserved it since she's been by my side since the sandbox.

"I'm sorry." Caroline said meaning it wholeheartedly.

"It's okay. I'll get past it and I'll meet a guy who actually wants to be with me." I told her trying to assure her. Caroline nodded and sighed.

"I just wish this would have worked out for you." Caroline said.

"Me too but it's okay." I told her again. Caroline nodded and I told myself not to think about him. It wasn't good for my health.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Damon POV**

"So you two should be my wing men so I can ask her out." Mason suggested. Klaus looked at me and I shrugged. I had to pretend that everything was cool or else Mason would figure out that there was something off about me.

"Whatever." I said and Mason grinned and stood up. 

"Watch how it's done boys." He said as he began walking across the quad to where Elena and her friends were sitting.

"Good luck." I said to him completely certain that she wouldn't say yes to him. Even I had to fight tooth and nail to get her to go out with me.

"I don't need luck. My talents are legendary." Mason said as he approached the table. Elena's eyes flared when she saw me and she stared at me questioningly. I focused my attention elsewhere, I couldn't look in those beautiful brown eyes or else I would possibly give up and ruin her life and reputation forever.

"Can I help you?" She asked the three of us. I noticed that she tried to keep her gaze away from me.

"Actually yes. I think you should go out with me." Mason said attempting to be smooth. Elena's eyes widened and they flashed over to me. I stood stoically by, not willing to let my own opinions influence anything.

"You want to take me out?" She asked her eyebrows raised until they were nearly touching her hairline.

"Yeah. You'll have fun baby. I'll make sure it's the best night of your life." Mason told her laying it on thick. I wanted to gag at the way he was acting towards her but I had to keep my reactions normal.

"You're going to give me the best night of my life?" She asked. I couldn't' pick anything out from her tone, she didn't sound incredulous or happy. I didn't understand.

"Sure am sweetheart." He told her and I actually rolled my eyes this time. Klaus was standing beside me trying desperately not to focus us attention on Caroline who was sitting right beside Elena.

"Well then. Fine. I've already went on one date with a guy who promised to give me the best night of my life. You can't possibly do any worse." She said.

"Well good. I'll pick you up at seven on Friday." He said.

"No, I'll meet you at the Grill on Friday at seven. Nothing is going to happen that involves you knowing where I live." She told him and I breathed a sigh of relief. She had no intention of sleeping with him which was good. But that really didn't explain why she was going out with him.

"A girl who knows what she wants. I like it. I will see you Friday at seven. At the Grill." He said and he motioned for us to walk away.

"Hey it really doesn't mean anything that she's going out with him." Klaus told me as we walked back a little ways behind Mason.

"She's going out with him. That is not a good thing." I told my best friend.

"If you want to hear what I think..." He trailed off.

"Fine, shoot." I told him.

"I think she's trying to make you jealous. I think she wants to push you to declaring your feelings for her." Klaus said.

"Maybe but I don't think that's it. I think that she said yes because she's trying to get over me." I told him and Klaus shook his head.

"That's not it." Klaus said as we sat down. I wished I could approach her about it, but I couldn't. We were over and I had no one to blame but myself.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Elena POV**

"I'm going out." I called to my parents Friday night.

"Where are you going?" They asked my before I left the house.

"To the Grill with Chloe." I told them which wasn't technically a lie. She was picking me up, taking me there and waiting for me to be done. She was going to be there the whole time, just not at the same table as Mason and I. I couldn't believe I said yes to Mason Lockwood. I couldn't stand the guy but I still said yes. I knew I only said yes because Damon was standing behind him and I was trying to prove to myself that I was over him. Which by the way I so am not. One just doesn't get over Damon Salvatore. I suddenly feel like one of those girls who he's slept with and dumped aside from the fact that we've never slept together.

"Have fun." My dad called. He was back to implicitly trusting me, something that I was happy about. My life finally felt like it was going back to normal after the Damon Salvatore debacle.

"I won't be late." I told them before leaving the house where Chloe was waiting. I got into the passenger seat of her car and shut the door before she pulled away from the curb.

"I still can't believe you're going out with Mason Lockwood. Are you going after Klaus next?" She asked me but I knew she was teasing.

"Nope, I'm only going out with Mason because he asked me. I have no interest in him and I really should have said no." I told her.

"But Damon was standing there and you had to show him that you were over everything." She finished for me and I nodded my head.

"Exactly." I said.

"I can understand that." She told me as we drove through town.

Mason's car was already there when we pulled up as was Damon's

"I guess he needed his wing-man tonight." Chloe noted.

"Apparently. That is going to make this so much harder. I can't look into his eyes and pretend to have fun with Mason. I'm going to fail miserably." I told her sighing audibly.

"He probably won't be at the same table. He'll probably just be sitting at the bar watching Mason. And you." Chloe told me and I nodded. I could do that. I could go through with a date that I didn't want to be on and I could ignore the only guy I wanted to date. I could do it. I knew I could. I walked inside and immediately found Mason sitting at the same table Damon and I sat at on our first and only date. The difference of the two occupants was comical. Both were good looking but Damon was so much more than just his looks.

"You came. I was beginning to think you weren't going to show." He said as I sat down.

"It's a woman's prerogative to be late." I told him inserting a smile onto my face. I wanted to show Damon that I was over him and I was moving on one way or another.

"I suppose it is. So I promised you the best night of your life and I'm going to deliver." He told me and I continued smiling no matter how fake it was. Damon was far enough away that he couldn't hear our conversation but maybe if he saw me smiling and appearing to have fun he would just assume I've moved on.

"Oh you are are you? You have high expectations of yourself don't you." I said rolling my eyes while continuing to smile. The smile had to stay on my face or else he would see right through me.

"I do. I'll do so much better than Damon did. You'll actually wake up in my bed tomorrow morning." He told me and I rolled my eyes.

"Oh you think so do you?" I asked him fighting myself on just walking away from this date now, damning the consequences. I did not want to be here. I really didn't want to be here. This was the worst decision I ever made. Bad idea Elena.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Damon POV**

Okay, I've seen enough. I've spent the last hour here watching her smile at him and seeing his confidence rise further and further. I was still convinced that there was no way in hell that she was going to sleep with him but I didn't like the way she was smiling at him. He wouldn't be afraid to take her out on another date. He didn't like her enough to care about what it would do to her reputation. Elena was the girl who I would never have again because I royally fucked it up. I drained my beer that I got thanks to a little bit of flirting and stood up leaving a ten on the counter.

"Dude where are you going?" Mason asked.

"I'm done here." I told him as my phone started ringing. I saw Klaus's name and answered it.

"What's up?" I asked him. 

"_I'm rescuing from pining after the girl on a date with Mason. Come on over. Mama brought home food from the restaurant for dinner and we have lots. Since you know it's only me and her.." He told me. _

"Done. I'll be there in ten." I said disconnecting the call.

"_Good. My mom told me if I didn't get you here she was grounding me for life. I will never understand why she likes you more than me." He said and I could practically see him shaking his head. _

"It's because she doesn't have to see me everyday and she didn't give birth to me. Ten plus hours of labour sometimes makes you dislike someone more." I reminded him.

"_Yeah yeah. Get here soon, mama won't let me eat until you're here." Klaus said before hanging up on me. _

"Gotta go. Mama Mikealson brought home food that she's sharing with me." I told Mason before walking away.

When I pulled up in front of Klaus's house I got out and walked right in without knocking.

"Mama Mikealson." I greeted her when I walked in.

"Hello dear. Come on in. Niklaus is getting impatient." She told him reaching up on her tiptoes to kiss my cheek. Klaus's mom was like a surrogate mom to me. She always made sure to make me feel like one of her own since she knew how shitty my home life was like.

"I'm sure he is. He's a growing boy." I said laughing.

"Stop talking about me and just eat." Klaus called from the dining room. Mama Mikealson was a short, chubby woman with a curly mess of hair. She was the complete opposite of my mom and I loved her more. She owned the most popular restaurant in town, it had a waiting list of a few months which was incredible. It was all of her family restaurants and it was fairly reasonable in price. It was the date destination of Mystic Falls due to the soft lighting and candles on every table.

"Yes yes, I'm coming." I told him as Mama Mikealson and I walked into the dining room where Klaus was seated.

"Take a seat dear and tell me everything that's new with you. You haven't been around in a couple of weeks, I was beginning to worry." She told me as she allowed me to dish up first. I grabbed my food as I pondered what to tell her. I didn't want to tell her I was completely into a girl when there was a chance that she would never see the two of us together. I was more apt to introduce a girl to Mama Mikealson before I introduce her to my own family.

"Damon's in love." Klaus interjected and I shot him a death glare.

"You're in love? You met a girl? Aw that's so sweet. I'm so happy for you. Tell me all about her." She told me her blue eyes shining happily at me. I always felt loved when I was in that house. Mama Mikealson raised five children by herself after her husband walked out after Rebekah was born.

"I'm going to kill your son. I didn't want to tell you because nothing is going to come of it." I told her and watched her face fall. 

"Why?" She asked me.

"He's too scared to be exclusive with her." Klaus shot in again with a smirk on his face. Those two had a really bad habit of talking about me like I wasn't there. But I knew they did it out of love.

"Damon you have nothing to worry about. You have so much to offer a girl, especially one that you love." Mama Mikealson told me.

"It's too late now. She's on a date with Mason Lockwood." Klaus told her and I shook my head. Mama Mikealson was going to know the whole story before too long including how I only wanted her because I wanted to sleep with her. The worst part was that I wasn't going to be the one to tell her any of it.

"Oh Damon dear, Mason Lockwood has nothing on you. Don't let him steal the girl that you're in love with. What's her name?" She asked turning to face Klaus again.

"Elena Gilbert." He said and I shook my head. Neither of us could have secrets from Mama Mikealson.

"Ooh Caroline's best friend. I see why you endorse that relationship." Mama Mikealson enthused and I had the pleasure of seeing Klaus's face go beet red.

"Yes, ironically enough." Klaus allowed.

"Now, Damon do you really care for this girl?" Mama Mikealson asked and this time Klaus didn't answer for me.

"I do." I admitted.

"Well then you should do everything in your power to get her back." Mama Mikealson told me.

"How do I do that?" I asked.

"Well first you have to tell me why the two of you aren't together." She told me and I sighed.

"Alright well we went out but you know me, I don't do exclusive relationships. I was only with her and I never cheated but I also demanded that we keep it a secret from everyone. I didn't want anyone to know. So she told me that she couldn't do it anymore and I told her I couldn't go public. The end." I gave her the quick version of our relationship.

"Why wouldn't you want to be public with the one girl you actually care about?" She asked me.

"Because I don't want her lumped in with all the other girls I've taken advantage of. I don't have a good past and my reputation really sucks. I didn't want any of that to rub off on her." I explained.

"That's noble but very stupid. You deserve to be happy and you're free to change your reputation. You just have to do it. If Elena wants to be with you she won't care. She will show everyone what a good man you can be." Mama Mikealson told me.

"See that's what I've been trying to tell him." Klaus interrupted.

"You can go do the dishes Niklaus." She told him and I laughed at the expression on his face. I loved watching her put him in his place. It was hilarious because he always obeyed without any argument. He respected his mom and it showed in the way he treated her.

"But Mama, this is an important conversation involving my best friend." Klaus whined.

"Nope, go do dishes." She said pointing to the kitchen. He sighed and gathered up the dishes while she focused her entire attention on me.

"But I already burnt that bridge. She won't want to have anything to do with me." I told her.

"Not necessarily. You just have to try. Give her no choice but to go on a date with you. A real date where you go somewhere in public." She told me.

"What would you suggest?" I asked her.

"If it's something you'd be interested in I will get you a table in my restaurant." She told me.

"It's booked up for something like six months isn't it?" I asked.

"Yeah but that's the perks of being me. I will get you a table for next Friday at six thirty of seven. That'll give you enough time to get her to go out with you." She told me.

"And you would do that for me?" I asked her.

"Absolutely. You're like one of my own. I want to see you happy." She told him squeezing my hand.

"Thank you. So how do I get her to go out with me?" I asked. This was going to be the hard part. I didn't know how to do it.

"Just show her how sorry you are. Buy her flowers tomorrow at school. Roses are best." She said.

"Elena's not a rose person." I told her. 

"What kind of flowers does she like?" She asked me.

"Daisy's. She loves flowers that appear to be wild." I told her.

"So do that. Just show how dedicated you can be. Make sure everything you do is not in private. You don't want her to think that you only want her in private again." She instructed me. I nodded and listened to everything she told me knowing

I needed all the help I could get.

"You can do this Damon. I have total faith in you." She told me.

"Thanks Mama Mikealson. But I should head home. I'm going to need to mentally prepare for tomorrow." I told her.

"You'll be fine. You have to promise me that once she's your girlfriend you'll bring her by. I want to meet the girl who's tamed my favourite guy." She told me and I smiled.

"Of course. Your approval means more to me than my own families." I said. She smiled at me and summoned Klaus from the kitchen.

"Your friend is leaving. Say goodbye." She said.

"See you at school tomorrow." He said.

"Yeah. I'm bringing my A-game tomorrow. Mason isn't going to stand a chance."


	7. Time Bomb

**It's a short one, I know but the next one is the date. I can't wait to write it, it's going to be a longer chapter. Possibly double this one. As always let me know what you think. **

* * *

**Elena POV**

After virtually running out on my date with Mason just minutes after Damon left the restaurant, I was not looking forward to facing him today at school. I really didn't care how he reacted, I just wanted it all off my back. I didn't want anything to do with him mainly because he wasn't the one I was falling in love with. Reluctantly I might add. I couldn't deny the intensity of the feelings I had for one Damon Salvatore. But I was trying desperately to. I didn't need his drama and his issues becoming a part of my life. Every girl wishes she can be the one to save a guy, but that girl obviously wasn't me for Damon Salvatore. When my dad dropped me off in front of the school I got out and sad goodbye. Of course the minute my dad drives away Mason appears. I was really hoping to avoid this conversation for as long as possible.

"So you ran out on me Elena." Mason said smoothly when he was standing beside me.

"Sorry about that." I told him hoping he would leave me alone.

"You know I'm not going to give up right?" He asked me.

"I wish you would." I muttered with my arms crossed.

"You're just afraid that it's going to end up being me. You're just trying to prolong the inevitable." He told me before walking away.

"Ugh." I sighed before following him onto the quad. When I saw my table I veered off and plopped down with an expletive and a sigh.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Damon POV**

I am freaking the fuck out. Completely. The flowers sitting on the passenger seat of my car feel like a ticking time bomb that's going to explode in my face any second now. This was completely stupid. Maybe I should have gone with the roses, like Mama Mikealson suggested. Maybe I should do this somewhere in private. But I knew that was a bad idea. My need for privacy was the reason I didn't have her now. What if she actually went through with it with Mason Friday night? What if she was now his girlfriend no matter how temporary that would be. I was seriously freaking myself out more and more and it definitely wasn't healthy. I am Damon Salvatore and the possibility of rejection should be considered impossible for me. But I was in serious danger of being rejected in front of all my peers. I could see it now. She would turn me down and I would be embarrassed. I didn't take embarrassment well since it had never really happened before. I always got what I want, it was a skill most guys wanted. I just hoped it worked that way today too, but that didn't usually happen for me.

I was parked in my usual spot in the student parking lot and I still haven't moved. It was ten minutes to the bell and I still had no idea how I was supposed to get out of this car where I'm safe and walk over to enemy territory and put my heart on the line. It seemed impossible and I had no idea how to deal with it. People were walking by the front of my car heading onto the quad looking in, confused as to why it appeared I was thinking about making a quick getaway. I heard a knock on my window and I snapped to attention. Klaus was standing on the other side with a smirk on my face, it was clear he understood the expression on my face. It was terror plain and simple.

"What are you doing?" He asked me when I rolled down my window.

"Trying to find courage." I admitted. He was the only one I would ever say that too. He was the only friend I had that wouldn't judge me.

"Good luck. So you're giving her those?" He asked gesturing to the flowers.

"I have until Friday to make her go out with me for real. That time line is feeling pretty steep at the moment." I told him shaking my head.

"Dude you need to have more confidence. I'm sure she'll say yes. My mother predicts that she's going to say yes too." Klaus told me and I smiled.

"Mama Mikealson always has my back." I smiled.

"Right before I forget she sent you breakfast too. You're supposed to eat before you go and talk to Elena. She gets annoyed that you don't eat breakfast." Klaus told me. I sighed and rolled my eyes taking the homemade breakfast sandwich from him and eating. That woman was like a mother hen. She wouldn't ever let me starve. I adored her. Besides her breakfast sandwiches were to die for.

"Tell your mother I adore her." I ordered him and he chucked.

"She knows." He told me as I finished off the sandwich.

"She deserves to know. She's probably the only woman on the planet that loves me for me." I shrugged.

"Probably. Elena would have you know if you hadn't screwed that up with out of place fear." Klaus reminded me and I glowered.

"Shut up. I have to go. I got to get this done." I said taking off my seat belt and opening the door. I was honestly contemplating making a clean getaway and not doing this. But I knew it wasn't an option. I had to talk to her. I had to have her. She was mine.

Ignoring all the curious glances as I walked across the quad with flowers in hand, I walked directly to Elena's table where she was laughing with her friends. I cleared my throat when I stopped behind her and she turned her head, her smile disappearing. I wanted that smile to grace her features permanently. I didn't like this unreadable expression that was on her face right now.

"Damon?" She questioned when I had been standing there for a while without speaking.

"Uh... hi." I greeted her stupidly. Elena's eyebrows raised and she stared at me trying to persuade me silently to start speaking.

"Hi..." She greeted, eyeing and the flowers in my hand. Everyone else at the table had lapsed into silence, presumably to ensure that they could listen to me make an ass out of myself.

"So how was your date with Mason?" I asked despite myself.

"It was fine. Is there a point to this Damon?" She asked.

"Uh yeah." I tried again.

"Why are you talking to me with other people around Damon? I thought that was against your rules." She asked me pointedly.

"Rules are made to be broken." I told her and she shook her head.

"You should have thought of that before." She told me as she stood up.

"Elena don't walk away." I called to her as she started walking away.

"Why not? What are you trying to accomplish here Damon?" She asked not caring that half the school was watching us now. To be honest I didn't care either. I wanted all of them to know that I wanted to be with her all the way. I wanted to walk onto the quad holding her hand in the mornings, I wanted to walk her to all of her classes. I wanted to be the one taking her out on dates somewhere everyone can see us. I don't want to hide what we have anymore.

"I want you." I told her stopping in front of her.

"We've already established that. I just won't be with you the way you want to be with me. I can't be a secret." She told me

"I don't want that anymore. I want you, all of you. I want you in public and in private. I don't want to hide with you anymore." I told her.

"I can't do that again Damon. I can't be your dirty little secret again." She told me and I finally had a grasp of how much it hurt her.

"I wasn't keeping you a secret for me Elena, I was doing it for you." I told her taking a tentative step towards her.

"How the hell do you get that? You did it for you because you didn't think you could handle a public relationship. You did it because you were scared and I was stupid enough to go along with it." She hissed, her temper flaring up now.

"No, I did it because I didn't want you lumped together with all the other girls I've been with. I didn't want you compared to Sophia because there is no comparison. But the second you and I got seen together you would become one of those girls. I didn't want that for you." I told her getting pissed off. The flowers were dangling from my hands and I had almost forgotten about them.

"Don't you think you should have let me make that decision for myself?" She asked me.

"I made a mistake, a very wise woman told me that I was stupid in almost those exact words. She told me that I would be an idiot if I didn't go after the one girl I actually want a real life relationship with." I told her and I saw her eyes start to soften.

"Why me Damon?" She asked and I had no idea how to answer that.

"I don't know how to say that. But in short it's everything. You challenge me to be better than I am. You want more out of me than anyone else does. You're beautiful. Elena Gilbert, I'm crazy about you. I'd have to be to be doing what I'm doing now." I told her and I swear to God there was at least a small smile on her face. Her lips were just slightly turned upward.

"Why now? Why right after I go on a date with Mason?" She asked me.

"You're too good for Mason. Hell you're too good for me. But Mama Mikealson told me basically to get my head out of my ass and get my girl back." I told her and she smiled.

"Who is Mama Mikealson? She sounds like someone I would like to meet?" She asked and I grinned. My Elena was back for the most part.

"Mama Mikealson is Klaus's mom. She's practically my surrogate mom and she arranged a date for us." I told her.

"You were so certain of yours skills that you had her plan us a date? What makes you think I'm going on a date with you?

You hurt me." She asked me and I shrugged.

"I'm not overly worried. I have five days to make you say yes." I told her and she raised her eyebrows.

"Oh you do, do you?" She asked.

"Yep, we have a table reserved for us on Friday night at a restaurant thanks to Mama Mikealson. I'm not telling you which restaurant because it's a secret. But you have to be there with me on Friday so what do you say?" I asked her.

"Hmm, no." She told me and my mouth dropped. I wasn't expecting that at all.

"No?" I asked.

"Exactly. You heard what I said." She told me. My girl was being feisty. I won already and she knew it, she just wasn't willing to give in just like that.

"I did. What if I give you these flowers? Will that change your mind?" I asked handing the flowers to her. She smiled and took them, sniffing them delicately.

"No. I'm not that easy Damon Salvatore." She told me with a smirk.

"Damn. So what do I have to do to make you go out with me on Friday night?" I asked her.

"I guess you'll have to figure that out for yourself." She told me reaching up and kissing my cheek before walking away. I watched her walk away from me with a completely dumbstruck look on my face. Oh yes, she was definitely my girl. I figured that was good progress for now so I walked over to my table where Klaus and Mason were watching.

"Good work." Klaus said grinning at me.

"Thank you." I said.

"So what did you say to her to make her kiss your cheek? She won't even touch me." Mason demanded.

"That is really none of your business. It's my turn again." I told him making it clear that he wasn't allowed to go after her.

"Who said you got another chance? You blew your last chance." Mason demanded.

"It involved a lot of grovelling, some daisy's and my charm." I told him shrugging.

"You know it will be me right. I'll be the one to take her virginity." Mason told me not appearing to be overly concerned.

"Maybe it's not about that for me anymore." I shrugged.

"You're actually serious about a chick? Come on Damon Salvatore doesn't do girlfriends." Mason laughed.

"Maybe Damon changed." Klaus interjected and I grinned at my best friend.

"Maybe but I can't see it." Mason laughed. I brushed it off and grabbed my bag knowing the bell was about to ring. I left the table and walked towards the doors seeing Elena talking to Matt "Wonder-jock" Donovan. If I was dating her, I was going to have to learn to be nice to him. I was just going to walk past her but as I passed by she grabbed my arm and stopped me.

"You know Damon right?" She asked Matt and we both stared at her. She stared at me pointedly and I knew it was a test. Last time we were out together, I was kind of a dick to Matt and she expected me to rectify that. She was never going to

stop changing me for the better.

"Yeah, I know him." Matt said stiffly. It was no secret that he hated me, I was never all that nice to him. Not that I was nice to anyone besides Elena and Klaus. "Are you guys dating now?"

"Not yet. That's totally up to him. He's got to prove some things to me first." She said eyeing me. I decided in that moment to swallow my pride and talk to the jock. Not my idea of a good time but hey. A man's got to do what a mans got to do.

"Matt. Uh... good game last week." I said completely awkwardly.

"Like you watched." He scoffed.

"I was mostly watching the cheerleaders, but even I could see that you did good." I said happy to be able to partially tell the truth. Elena smiled at me and that made this infinitely easier.

"I figured. But thanks anyway. I'll see you later Lena." He said before walking away awkwardly.

"Good work. You were almost nice to him despite how much it pained you." She said grinning.

"It was painful, but anything for you." I said rolling my eyes.

"Good. I want to meet this Mama Mikealson." She told me and I laughed.

"Ha, not until you go on a date with me. You go out with me and I'll take you to meet Mama Mikealson. That's my deal.

No one introduces their parents biological or otherwise to someone they haven't even taken out on a real date yet." I told her.

"Fine. I'll go out with you. This better be some date Damon." She warned me.

"Don't worry it will be." I told her before walking away.

"It better be." She called after me again with a laugh.

"You just had to have the last word didn't you?" I asked and she laughed again.

"Yup. But now I think you should walk me to class." She told me and I grinned.

"Absolutely." I said walking back to her side and slinging my arm over her shoulder as we walked down the crowded hallway.


	8. Best Night Ever

**Here is a considerably happier update as compared to ETU. Enjoy Delena's first date.**

* * *

**Damon POV**

It was Friday night and here I stood in front of a mirror in my bedroom pondering whether or not I looked good enough to even bother taking Elena Gilbert out for a real sit down, flowers at the doorstep kind of date. After changing my outfit around six times I had finally decided on a blue shirt and black jeans with my usual boots. Blue because once Elena commented on how much she likes blue shirts on me, the rest because I really didn't want to look like I was trying too hard. Even though in reality I was trying. I was trying so hard. I have never ever tried this hard at something before aside from my grades, but right now even my grades seem to be taking a backseat to these feelings I have for one Elena Gilbert. I glanced at the clock on my cell phone and took a deep breath. It was time. I had just enough time to stop and get some flowers before I went to pick her up. I had every intention of being right on time. I was actually making the effort to impress her parents. I had a long way to go, my reputation really has preceded me and I'm sure Dr. Grayson Gilbert knows all about it. He's probably lecturing his daughter right this very minute about why she shouldn't be going out with me. It's okay though, I can take it. I can handle a little bit of parental disapproval if it means I still get the girl. I left my room, shutting the door behind me, my family as a strict no opening of bedroom doors unless it's your own rule and I'm thankful for that. If anyone in my family had ever walked in to find me doing what I did on a regular basis with different girls every night, they would be disgusted and disappointed.

"Where are you off to?" My dad asked as I grabbed my leather jacket off the hook and my keys out of the bowl beside the door.

"I have a date." I answered as confidently as I could.

"Are you coming home tonight?" He asked always the father. He needed to know where I was because he honestly worried about me. It felt nice to have one parent who worried about your well-being for no other reason than just being a parent.

"Yeah." I answered.

"Alone or with a companion?" He asked and I chuckled. He knew exactly how I worked and he never really tried to stop me because he knew it was futile. He figured I'd grow out of it all on my own. He was right.

"Alone. It's a real date dad." I told him not really expecting the smile on my dads face when it came. He didn't smile too often, he was a stern parent who liked to let us make our own decisions.

"Really? Wow, son I knew you'd grow up eventually. I can't wait to meet this young lady who has you changing." Dad said and I grinned in response. It wasn't often that my dad was even partially proud of me. That was more Stefan's gig than mine.

"You will at some point I promise. I need to make it through this date without ruining it first." I told him and he nodded knowingly.

"You'll be fine, that first date is always the hardest. But once you pick her up it'll be as easy as breathing if the chemistry is there. If it's not then make sure there isn't a second date. No use torturing each other longer than necessary." Dad advised.

"Oh believe me the chemistry is there. We were seeing each other for a couple of weeks without anyone noticing before she decided she needed more than that. We have tons of chemistry. The only thing I worry about is her realizing that she can do so much better than me." I admitted. Usually I refrained from showing any sort of emotion around my dad, but it seemed fitting with the conversation we were having despite the fact that I really needed to go.

"What's this amazing girls name anyway?" He asked and I grinned.

"Elena Gilbert." I answered proudly because any guy who got to call her his girlfriend was a lucky one. I can't believe I almost lost her because of some stupid fear. There is no way anyone could ever lump her together with any of the other girls I saw, mainly because they will see beyond a shadow of a doubt that I actually have feelings for her.

"Ah yes, Dr. Gilbert's little girl. Good luck son. What time are you picking her up?" He asked and it was my cue.

"In about half an hour so I better get going so I can get some flowers. I can't pick my girl up at her house with her parents there without some flowers to impress them all with." I said and my dad nodded.

"Have fun tonight and I'll see you when you get home." He said finally dismissing me. My father and I didn't have too many candid conversations like that one and it quite honestly felt really good when we did. It was times like these that I remembered that I actually have a father.

"Yeah, I'll see you tonight." I told him as I walked out the front door shutting it firmly behind me.

When I got to the flower shop, the elderly lady at the counter smiled at me. I wondered how many nervous teenage boys she had seen come in here to get flowers.

"You're going to buy out all the daisy's in the entire state of Virginia if you keep this up." She told me as I carefully chose the most perfect bouquet I could find.

"My girl deserves every daisy in the state of Virginia." I told her as I selected the most colourful bunch. They were pink, orange and yellow. The colours were bright and the flowers were perfect as far as I could tell. I wasn't exactly an expert with flowers, the three times I bought flowers for Elena were literally the only three times I have ever bought flowers.

"It's guys like you that make my business so successful. The girls that you guys are with are the luckiest ones. So keep doing what you're doing and she'll never be able to break up with you." She told me and I grinned.

"I hope not, this is technically our first date." I laughed as I handed over some cash to pay for the flowers.

"Well good luck to you both." She said as Damon left the store. He carefully put the flowers in the passenger seat of the car and drove towards Elena's house. When he finally arrived he took a deep breath and turned off the car. He was three minutes early so he got out and walked up the front walk.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Elena POV  
**

When I heard the doorbell I started panicking. I was ready aside from a small issue with my shoes. He told me to dress nice via text message today so I assume that means a dress and heels. The only issue is I can't find my sole pair of Louboutins that my parents bought me and I really need them tonight. They were my good luck shoes and I needed them on this date. They made my legs look amazing not that I really needed the help. Caroline told me on a regular basis that my legs were to die for.

"Are you almost ready for your big date sweetheart?" My mom asked at my bedroom door.

"I can't find my shoes." I wailed after having torn my closet apart looking for them.

"Which ones?" My mom asked opening my bedroom door and coming in.

"My black Louboutins. The ones with the red sole." I told her as I frantically rushed from my room and ran to Jeremy's to

see if he stole them from me to be mean.

"I haven't seen them, have you checked downstairs?" She asked and I shook my head after exiting Jeremy's room after making him promise that he didn't have my shoes.

"You better hurry sweetie, your dad is down there with your boyfriend." My mom told me and I instantly panicked. I worried that dad would send Damon running for the hills.

"I'm trying but I can't find my shoes." I screeched as I ran from my room with the flowy fabric of my dress billowing behind me.

"Are they downstairs?" Mom asked me as she found me in the hallway.

"I don't know. Are they?" I demanded and my mom chuckled in response as she walked downstairs.

"Come and check. You should let your boyfriend know you're not ditching him." She said. I sighed and walked towards the stairs when Damon's voice greeted me.

"Is everything okay?" He asked with humour in his voice.

"I can't find my shoes." I sighed ready to give up and stay home.

"There are some black heels poking out of the closet." He called to me and my spirits perked up immediately.

"Do they have a red sole?" I asked eagerly. I heard him pull them out of the closet and answer with a yes. When I heard that word I ran down the stairs as quick as I could to get the shoes from him. Crisis averted. He found the shoes. Thank God.

"Thank you so much." I said wanting nothing more in that moment to kiss him, but she knew her dad wouldn't appreciate her laying one on Damon when they hadn't even went out yet.

"No problem. Wouldn't want us to miss our reservations." He said as I slipped my feet into the high heels.

"Be home by ten." My dad told me seriously, and Damon nodded solemnly.

"Yes, Dr. Gilbert." He said seriously. My dad nodded as if he wasn't impressed. He had tried to talk me out of dating Damon for the past few days but I couldn't change my mind. I wanted nothing more than to be his one and only. I knew though that dating him I was going to have to go much further than I ever did with Matt. He wouldn't be able to be celibate with me forever. Eventually he was going to want more from me and I expected that. He led me out of the house and he actually opened the car door for me before I got in. I was highly impressed by his actions and I knew my mom and dad were watching from the window. I could imagine the impressed look on my moms face and the complete opposite look on my fathers.

"So where are you taking me?" I asked when we began driving.

"Well a little place I would like to call Mikealson's." He told me and my eyes widened.

"You're taking me to Mikealson's? How did you manage that?" I asked completely shocked.

"I called in a favour. Klaus's mom is the owner of the restaurant. She basically gave me no choice but to take you there." He told me and I smiled impressed.

When we got to the restaurant, he opened my door again and took my hand. When he led me inside he was immediately escorted to a table.

"Good service here." I said when we were seated.

"Mama Mikealson probably saw us come in and told the guy to seat us right away." He told me and I nodded impressed with him. After we ordered we talked some more, he was really easy to talk to. We just had that connection and I loved it. I had never had that connection with anyone before. Matt and I had amazing conversations but we never had that sexual connection Damon and I have. Dinner once it arrived was delicious. I had never tasted anything like it.

"Mama Mikealson has been teaching me to cook every time I've been over there for dinner." Damon explained.

"You like cooking?" I asked him amazed to learn something else.

"Yeah, it's a bit of a guilty pleasure." He admitted. Once we were done eating he paid the bill and we left.

"So where are we going now?"I asked him.

"I thought we would go back to where it kind of began for us. The Falls." He told me and I nodded happy with that idea.

"I love that idea. What are we going to do there?" I asked.

"We'll figure it out when we get there." He said as we walked back to his blue Camaro.

When they got to the Falls he turned up the radio in the car and got out to sit on the hood. I got out and joined him.

Before I sat down one of my favourite songs started to play.

"Want to dance with me?" I asked him and he smiled standing up and taking my hand. He pulled me into his embrace, his hand on my lower back, the other one holding mine. My hand went to his shoulder and we started moving.

"You're a good dancer." I told him as we swayed to my song.

"My mom taught me. One of the only useful lessons she's ever taught me." He said softly.

"I'm sorry your mom is not one that you can depend on." I whispered.

"It's not your fault." He whispered my head on his shoulder.

"I just think you deserve everything. You deserve so much more than what you've been given. No one knows just how special you are." I whispered.

"There is no one like you Elena Gilbert." He whispered before he tilted my chin up to kiss me passionately. We stopped moving as we kissed, his other arm wrapped around my waist, bunching my dress up slightly. His other hand cupped my jaw. His tongue plundered my mouth and at the moment there was nothing more that I wanted than to keep kissing him.

"I don't want to stop but I don't know how far I can go tonight." I said pulling away in need of breath.

"We'll stop whenever you want." He promised as we went to sit back on the hood of the car.

"I want to keep going but I'm not ready to have sex. I'm sure I will be soon but not tonight." I told him.

"I'll wait as long as you want. It's not why I'm with you Elena. But the second you want more I will give you more. Just not tonight." He told me. I understood that he was trying to make a good impression tonight.

"Not tonight but soon." I told him and he kissed me once more.

"Do you want to go get some ice cream?" He asked me and I smiled.

"That sounds perfect."I agreed and we got off the car and back inside.

After we had ice cream, Damon drove me home. He stopped the car outside my house and we both got out. He held my hand as we walked up the front walk.

"So you hold my hand and walk me to my door. You're pulling out all the stops tonight." I said with my hand on the door handle.

"Now I'm going to kiss you goodnight and leave." He told me and I smiled.

"You should do that." I said and he lowered his lips to mine, keeping this kiss chaste in case my parents decided to spy, which I was about eighty percent positive they were. It would be just like my dad to watch us out here to make sure Damon didn't do anything bad. When we broke the kiss, he gave me one more small peck on the lips before pulling back.

"Maybe I'll see you again tomorrow." He said and I nodded.

"Text me." I told him as I turned the handle.

"I had an amazing night, I'll text you later." He told me before turning and walking to his car.

"Goodnight." I called and he called the same thing back to me.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Damon POV**

When I walked in the front door I dropped my keys in the bowl whistling. I just had the most amazing night ever and I didn't want it to end.

"How was your night?" My dad asked from the sitting room. I walked into the room and he was sitting nursing a glass of bourbon with a book in his lap. Stefan was sitting across from him and he looked up clearly hoping that my evening with Elena failed.

"It was perfect. I'm having a hard time trying to figure out how I got so lucky. I did nothing to deserve Elena Gilbert." I told them with an actual smile on my face.

"You earned her somehow. There is something in you that she likes." Dad said and I smiled again.

"I'm probably going to see her tomorrow again." I told him and my dad nodded.

"You should bring her by sometime. I'd like to meet this girl." He said and I nodded.

"I will." I promised. Just as I started turning around to walk up to my room, Stefan rose and grabbed my shoulder.

"Don't you ever get tired to screwing up my life?" He demanded.

"Oh pray tell what did I do to you this time Stefan? Did I misplace your hair gel?" I asked him sarcastically. I really didn't need him screwing up my night. I was in a perfectly good mood thank you very much.

"You stole Elena from me. She's supposed to be my girlfriend." He hissed and I rolled my eyes in response.

"Elena is her own person. If she wanted to date you, you would be dating her." I told him sick of Stefan's childish antics.

"Sure she is. You probably needled her until she said yes." He whined.

"Why yes I did Stefan. But the difference between you and me is that I actually made an effort and she actually started to like me. I don't know why but she did and now I'm not giving that up for the world." He said firmly before turning and walking upstairs. This was the best night ever and there was no way Stefan was ruining it.


	9. Wanted

**I'm so sorry about the wait on this. my internet got cut off a while back and I haven't been able to update. Thank you for your patience and as a reward we have a bit of smut in this one. ;) Enjoy. I still have no internet so updates will come whenever I can steal a connection from somewhere.**

* * *

**Elena POV**

When I woke up the next morning, I rolled over and stared at the clock. I had nothing to do today and all I wanted to do was see Damon. We had such a good time last night that I wanted to continue it this morning and for the rest of the day. The only problem was I had to find a way to him. I would be getting my licence in just a couple of months but that didn't help me now. Sighing I got out of bed and walked downstairs where my dad was reading the morning paper.

"Good morning." He greeted me as I poured myself a cup of coffee. He started at me disapprovingly, he hated it that I drank coffee already.

"Morning, so can I ask you a favour?" I asked him.

"You can ask." He told me, making it clear that he had every right to say no. I guess that was true, but it would only take a couple of minutes of his time.

"Alright, I was wondering if you would take me to Damon's house this afternoon. I want to spend some time with him." I asked hopefully.

"Are his parents going to be there?" My dad asked.

"I assume so. Mr. Salvatore only works Monday to Friday." I answered.

"What time do you want to go there and what time do you want to come home? How are you getting home?" He asked me and I knew he found these questions important.

"A little later, I don't want to wake him up. I'll come home before too late and I assume he would drive me." I answered all

his questions.

"Fine I'll take you over there later. But you have to know that I don't like the idea of you hanging out with this boy. But I'm not going to stop you. You need to make your own mistakes." He told me and I nodded my head. I really appreciated my parents stance on not interfering in my business unless I really needed them too. They would let me date the wrong guy as long as I didn't get too hurt.

"Thank you daddy. I'm going to get ready." I told him kissing his cheek as I rushed back up the stairs. That was far easier than I expected. I thought he would have given me far more trouble than he did. When I got into my room I walked into the Jack and Jill bathroom that my brother and I shared, locking the doors on both sides. I undressed quickly and stepped under the warm spray.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

** Damon POV**

I woke up thanks to a glass of ice cold water being poured over me. I opened my eyes to find the smiling face of my best friend.

"What the fuck do you want? And was that really necessary?" I grumbled, mashing my face back into my pillow regardless of the fact that everything around me was completely soaked. It's official Klaus Mikealson is a dick.

"We're playing video games and you're telling me all about your date so I can pass the info on to my mother." He told me and I grumbled again.

"You couldn't wait until later because?" I asked as I reluctantly sat up. One thing I knew about Klaus was that he wouldn't leave until he got what he wanted, and honestly I wanted to tell him all about the date. It was the best date I've ever been on and that's quite a feat considering I've been on a lot of dates.

"Mama had me out of bed at 7:30, you should be happy that I waited until 9:30 to come here." He told me as he moved to the TV on the other side of my room. He sat in the two chairs that were around it and waited until I came to join him. I pulled myself out of bed and walked into my bathroom. When I came out a few minutes later he was waiting for me to play the game, both of our games set up and our controllers ready.

"Mama Mikealson is an evil woman. It's the weekend, we should be able to sleep for all hours of the day." I muttered as I sat down. Klaus didn't even give me the chance to go downstairs and get food before he started the game and his character was chasing mine trying to kill me.

"So date? What happened?" He asked and I smiled.

"It was the best night of my life." I told him.

"Good. Mama needs more than that. She told me not to let you be shy about it." He told me and I sighed. Those two knew me too well, I had to start keeping my distance. I couldn't have any secrets from Klaus or his mom.

"Fine. We went out to dinner and it was incredible like I knew it would be. Mikealson's food couldn't ever be anything less than amazing. But then we went to the Falls." I told him.

"Then bow chicka wow wow?" He asked, this words sounded hilarious in his accent and I laughed.

"No. We didn't have sex if that's what you're asking. We danced. One of her favourite songs came on and we danced in the headlight light. Then we made out. After that I took her home and kissed her goodnight. That was it." I told him.

"So no bow chicka wow wow? You didn't sleep with her and it was still the best night of your life?" He asked me with his eyebrows raised.

"The nearest we got to bow chicka wow wow was making out on the hood of my car." I told him shaking my head. My best friend was an idiot.

"I'm impressed. Mama will be impressed too, although I know she would have wished you could have kept it to a peck on the first date." Klaus laughed.

"I don't peck. And if I remember correctly she instigated the whole make-out session part of our evening. I was trying to behave." I told him.

"Good to know. Anyway I brought you food. Mama said not to give it to you until you gave us what we needed." He told me handing over a hand-packed bag of what I knew was a traditional Mama Mikealson breakfast. I couldn't count the times I'd left home way early on a school day just to get breakfast from Mama Mikealson. She was the best cook I'd ever met and sometimes I really wished I'd been born into her family. Klaus gave me a few minutes to eat the homemade cheese bagel with cream cheese, bacon, and egg with the hashbrowns done up in true Mikealson fashion before we resumed our game. I was pretty sure my primary reason for staying friends with the idiot known as Klaus was his mother.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Elena POV**

"Call me if you need a ride." My dad told me when he stopped at the long driveway of the Salvatore house.

"I will. I'm pretty sure he'll drive he home." I told him.

"Does he know you're coming over?" My dad asked me and I blushed.

"Not yet. I wanted to surprise him." I answered.

"It looks like he has company." My dad noted, gesturing to the black Charger in the driveway beside the blue Camaro.

"That's just Klaus." I told him shrugging.

"Alright, call me if you need anything." He told me and I nodded opening the door and walking up the driveway. When I got to the door I waved to my dad and he drove away. I knocked on the door and heard footsteps coming closer.

"Can I help you?" Mr. Salvatore asked when he opened the door.

"Uh I'm Elena Gilbert, I was wondering if Damon was home?" I asked shyly. Mr. Salvatore always scared me, he looked so hard and intense.

"Ah yes, you're the girl that Damon can't stop talking about. You've done an amazing thing, taming my eldest son. Come on in my dear." He said smiling broadly at me. I instantly felt myself relax around him, he definitely wasn't anywhere near as mean as his reputation said he was. Giuseppe Salvatore had the reputation of a no nonsense lawyer and a lot of people were afraid to get on his bad side.

"It's nice to meet you Mr. Salvatore." I told him still shy.

"Oh call my Giuseppe my dear. The boys are upstairs if you want to go find them. Just walk up the stairs and go right instead of left. He's the third door down." He told me and I smiled.

"Thank you." I said as I started walking up the stairs. When I got to the split in the stairs I followed Giuseppe's directions. The furnishings in this house were so ornate and old fashioned, I loved it. All the way up the stairs were pictures of Damon and Stefan through the years. Child Damon was one of the cutest things I've ever seen. I knocked on the door softly and was called inside by Damon's voice. He sounded distracted but I could hear the sound of video games in the background. I walked into the room and found him sitting on a chair in front of a big screen TV.

"Hi." I greeted him.

"Hey, I didn't know you were coming over." He said pausing the game and coming over to kiss me.

"I wanted to see you but I wanted it to be a surprise. Good surprise or bad surprise?" I asked not sure how he felt about me just appearing.

"Good surprise. You can come surprise me like this whenever you want." He told me and I pecked his lips once more.

"I don't want to interrupt what you're doing. I'll just watch you." I told him and he grinned.

"Come and watch me kick Klaus's ass. Now that I have support I might actually win." He told me taking my hand and pulling me over to the chairs. He sat down first before pulling me onto his lap.

A few minutes later Damon lost the game.

"Damn it. Baby you're not good luck at all." He complained while Klaus just laughed.

"She can't help it that I'm just way better at this game than you are." He laughed.

"You just shush. First you come over and pour water on me to get me out of bed and now you kick my ass at a game. I think you need to go before we're no longer friends." Damon told him.

"Oh come on. You couldn't not be my friend even if you tried. You would miss Mama's cooking too much and then you'd have to spend more time with Mason." Klaus told Damon and he was silent for a moment.

"Damon he makes a valid point. You wouldn't want to spend more time with Mason would you?" I asked.

"No I definitely wouldn't. I'm still irritated that he got to take you out on a date." Damon muttered.

"I went out with him to make you jealous." I told him smirking.

"It worked." He said and I kissed his cheek.

"I think I'm going to head out. Mama wants me home this afternoon so I can fix the stairs on the deck." Klaus said as he stood up.

"Do you want help? Elena and I could come by." Damon asked and I hoped Klaus said no. I wanted to stay in here with him.

"Nah, I'll be good. It'll only take a few minutes, a couple of the boards just came loose." He said brushing it off and I

smiled.

"Alright. Call if you want to do something tonight." Damon told him.

"I will. Feel free to bring Elena if we do something." He told him and I smiled. I liked that Klaus was including me in his plans with my boyfriend. Most guys wouldn't want their best friend's girlfriend going places with them.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~DE~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**Damon POV**

A little while after Klaus left, Elena and I had relocated to my bed and were making out rather intensely. My hands were slipping under her shirt and she wasn't stopping me. I was lying between her legs as we kissed and touched everywhere we could reach. Her hands were roaming all over my back under my t-shirt. I knew I wouldn't be able to continue for too long before I had to stop. I didn't want to pressure her. She wrenched her lips from mine to take a breath and I trailed mine down her neck, sucking and licking. I really wanted to mark her but I knew she wouldn't like that, or at least her dad wouldn't like it. She brought her hands out of my shirt and took my hands out of her shirt so she could sit up. She surprised me by pulling her t-shirt over her head leaving her upper body with only her bra covering it. Here I was thinking she was pushing me away having had enough. Her bra was cute, white with little pink and purple flowers. The innocent look was in direct contrast with the way she was sucking on my neck now. Her chest heaved as I threw my head back to give her more access. She pushed at my chest and I fell onto the bed. She climbed over so she was straddling my body as she continued sucking at my neck. She was clearly determined to mark me and I didn't care. I would proudly go to school with a hickey from Elena. She pressed herself down onto me and I groaned. I was so hard, I guarantee I've never been this hard before. Any other girl I've ever been with I've been able to get relief from but I was sure Elena wasn't ready to go there yet. But oh how I wanted to. I was pretty sure I was going to have zipper marks on my cock with how hard it was pressing against it. She trailed wet kisses up to my ear and sucked my lobe into her mouth. I was having a hard time remembering how innocent she is. She was coming up with all of this all on her own. Her body was moving against mine sinfully and I loved every second of this. She pulled away to take my hands and put them on her bra covered breasts. I didn't want to do it without permission, but now that wasn't a problem. I squeezed and weighed them in my hands. They weren't the biggest I've ever seen but they weren't the smallest either. They were the most perfect I've ever seen or touched by a long shot. She reached behind her and unclasped her bra and I almost died right then. She pulled the fabric away from her breasts and put my hands on her bare skin. They were even more perfect with nothing covering her but my hands. I didn't know where this came from but I didn't want it to stop.

"I don't want to push you too far." I told her and she smiled at me, sitting back on her heels so her denim covered core was pressed against my painful denim encased cock.

"Don't worry. I'll stop when I can't go any further. I'm not ready to have sex, but we can do other stuff." She told me and I nodded my head and swallowed hard. I didn't trust myself to speak, I was so turned on. Never before had a girl been able to get me so ready to come just by kissing me and letting my touch her tits. She moaned into my mouth as I squeezed one of her nipples between my thumb and forefinger. I flipped us over so I was on top of her. I needed to make her come but I was sure she wasn't willing to strip any further for me yet. It would all be on her time. I thrust my clothed cock into her and she moaned lifting her hips against mine. I had never dry humped anyone before and it wasn't anywhere near as good as skin on skin but it wasn't bad. We moved against each other and I played with her nipples. Her hands were on my back so I sat up and pulled my t-shirt off so she could touch my skin. I brought my head down and took one of her nipples into my mouth. She gasped and pushed her chest closer to my face.

"Oh my God." She moaned. I reached over onto my bedside table and put my Ipod onto the dock so the music covered the sounds she was making. I didn't want anyone else hearing this. I thrust against her once more before she came apart. I knew I had to go take care of my issue but I didn't want to move yet. She was sated and I didn't want to miss a moment of

it. I dropped my head to the crook of her neck and moaned. I was in agony.

"Wow." She said with a chuckle.

"Yeah, I'll be right back." I told her rising off of her. Every movement hurt and I needed to take care of this now. I had never been so hard.

"Where are you going?" She asked sitting up, still gloriously nude from the waist up.

"I need to go take care of myself. I need to come." I told her as I walked into my bathroom. At least I would have plenty of images to jack off too. Elena topless and Elena coming were at the top of my list. When I got into my bathroom I quickly stripped out of my pants and threw them into the corner opting to put my sweatpants back on when I was done. Just when I wrapped my hand around my base, Elena stepped into my bathroom.

"Can I help?" She asked me and I nearly blew my load right there. Hell yes, I wanted her to do this.

"Sure." I told her.

"What do I do?" She asked.

"Just take your hand and rub like this." I told her putting her hand on my shaft and moving it up and down at the pace I

liked. She smiled and I removed my hand so she could do it on her own.

"Why didn't you just keep rubbing on me until you came?" She asked me.

"I didn't want to come in my pants." I told her and she nodded. She picked up her pace on my cock and I moaned loudly. I was glad that the music was cancelling all of our noises out. I knew Stefan was gone and my dad was working downstairs so no one would interrupt. When I came I spurted all over her hand and she smiled. She pulled her hand away and I grabbed her a towel so she could wipe her hand off.

"Caroline told me I should taste it." She said idly as she studied her hand which was still coated in my come.

"She what?" I asked not expecting that.

"She said I have to taste a man's come. She said it tastes amazing. She told me she sucks Tyler off just so she can have his come." Elena said and I watched as she brought her finger up to her mouth and suck my come off of it.

"Elena..." I moaned already feeling myself harden again. This was so much more than I expected when she came over here today. She licked the rest of it off and wiped her hands on the towel.

"Salty." She shrugged. My dick was hardening again and I couldn't believe it. I just came and I was getting hard again, this girl would be the death of me.

"I want to taste you. Just say no if you don't want that." I told her, unable to believe just how much I wanted to put my mouth on her and drink her down. She nodded her head and her hands went to her jeans as she pushed them down. She left her panties on as she walked back to the bed and sat down.

"I don't know what to do." She said nervously.

"Just lie down. I'll take care of the rest." I told her reassuringly. She did as I said and I crawled onto the bed completely naked. I hooked my fingers in the sides of her skimpy panties as I kissed her lips making her feel comfortable. Her cheeks had a slight blush to them so I kissed her once more before going down her body. Eating her out was the only thing I wanted in the entire world right now. I decided to go easy on her and gently lick her letting her ease into the sensations I was evoking inside her.

"Oh God." She moaned as I brushed my tongue over her clit. Her body was already trembling and I knew it wouldn't take too much to get her to come again. I pushed one finger inside her and her eyes snapped open.

"I'm going to pump my finger." I warned her as I pulled it out and thrust it back in. She relaxed again and I licked her clit continuously.

"I want to suck on you like Caroline told me to." She told me and I felt myself get even harder. I reflexively thrust against the bed.

"No, not tonight." I told her.

"When?" She asked pouting.

"Tomorrow. We'll do it soon." He grunted. I blew a stream of air across her clit and she shattered. She moaned my name and flexed her hips. She was completely beautiful when she came.

When she came down she rolled onto her side to face me. My cock was so hard but I didn't want to go rub one out again until she came back to Earth.

"Do you have to go masturbate again?" She asked with a guilty expression on her face.

"I should." I said not wanting to leave her in my bed alone.

"Lie down." She told me and I didn't know what she was planning.

"Don't suck me off. If you do, I won't be able to stop." I warned her. She nodded her head and straddled my hips leaning down to kiss me. My dick was so hard it wouldn't take much to make me come. When she started running her pussy along the length of my dick I almost lost it.

"Elena, what are you doing?" I asked squeezing my eyes shut. She felt so fucking amazing.

"I'm getting you off. You need this." She told me as she continued moving. I let her do what she was doing knowing she was on birth control. I didn't want her to stop. Ever. When I finally came she pulled away from me and grabbed the towel from the bathroom to wipe my release off of my stomach.

"You're amazing." I told her as she lay down beside me.

"I don't want to leave this bed." She told me.

"You're always welcome to stay." I told her and she smiled.

"I'll get grounded but it's worth it. Even if I am grounded I'll find a way to see you. Or better yet I'll call Caroline and tell her to lie for me. I'll tell my dad that I'm staying with her." She said and I smiled. She was willing to disobey her parents for me. She was amazing. At the rate I was going it wasn't going to take me long to fall even more madly in love with her.


	10. Let's Make Love

**Elena POV**

I woke up the next morning to fifteen text messages from my mom and dad. I knew I had to call them but I really didn't want to move from this happy little cocoon I found myself in. Wrapped up in Damon Salvatore's arms while the window was open letting the morning breeze blow through was every definition of perfect. The sun was slanting through the curtains and he looked amazing even in sleep. I had wanted to stay awake later than him last night so I could study his features all night, something I was too embarrassed to do while he was awake. I wasn't at the point in our relationship where I could openly stare at hiim just because I wanted to.

"I can feel you staring." He murmured with his eyes still closed. His arms tightened around my waist and pulled me closer to him. I gasped when I felt his early morning hardness.

"How? You haven't even opened your eyes." I asked.

"I don't need to open my eyes to see you. I can feel your eyes on me." He said finally cracking open one eye.

"Well good morning there. He finally awakes." I teased. He responded by rolling me onto my back and straddling my body.

"You shouldn't tease me so early in the morning Elena." He warned me and I giggled.

"I should text my parents. Caroline was supposed to tell them I was staying at her house." I told him and he rolled off of me and I grabbed my phone from the bedside table. I opted instead to call home, knowing that if they wanted to yell at me it was better to do it over the phone instead of text message.

"Elena?" My dad asked when he picked up the house line after only one ring.

"Yeah it's me. I spent the night at Caroline's, I thought you knew." I told them.

"We know that now. I'm sorry for all the messages, we didn't get a hold of Caroline until this morning." My dad told me and I breathed a sigh of relief. I was so happy they bought our story.

"It's okay. I'll be home in a little while." I told him and my dad told me to take my time. It was Sunday morning and I had

all day to do whatever I wanted.

"Just call me when you want a ride, I'll come and pick you up." My dad told me.

"I was just thinking of calling Damon. I want to spend some time with him today before I come home." I told him and he agreed. When I hung up my phone immediately started ringing again. Caroline's smiling face popped up on my screen and I mouthed a "sorry" to Damon before answering it. He shrugged and started drawing shapes on the part of my arm that wasn't covered by his t-shirt.

"Hey." I greeted her happy that our plan worked.

"I think Tyler is cheating on me." She whispered. Her voice was hoarse so I knew she'd been crying. It wasn't too often that Caroline Forbes cried over a boy. If she thought something else was going on with any guy she was dating she'd typically just dump him and get it over with. But this was Tyler and she really liked him, maybe even loved him.

"Why do you think that?" I asked needing more information.

"I called him last night to see if he wanted to come over and he said no. I was okay with that until I heard the voice of another girl in the background. But now he's dodging my calls and he won't pick up the phone." She told me.

"Do you want me to come over?" I asked her, knowing that my duties as best friend involved comforting her in times of need. This was definitely one of those times.

"I don't want to interrupt your time with Damon." She said. I heard her sniffle and I knew without a doubt that I had to go to her.

"No you're not. You're my best friend, I'll be there whenever you need me. You need me right now, just let me change and get Damon to drive me over." I told her. She whispered thank you to me before we hung up.

"What's up with Caroline?" Damon asked getting the gist of who I was talking to.

"She thinks Tyler's cheating on her and she's really broken up about it." I explained as I got out of bed and grabbed my jeans and shirt. I quickly changed out of his t-shirt and back into my clothes while he dressed too.

"Tyler's been spending a lot of time with Mason lately. He's practically become an honorary member of our group. But I'm not sure what's going on there." He told me.

"It scares me that Tyler is spending time with Mason. Aside from you and Klaus, I don't like the rest of your group." I told him apologetically.

"Don't apologize. I'm not all that fond of them either." Damon said dryly as we left the room.

We made it out to his car without any interruptions. When we got into the car he turned up the radio and drove me to my best friends house.

"Am I going to see you again today?" Damon asked.

"I'll call you when I'm done with Caroline." I told him and he leaned over to kiss me goodbye. Before I even got to her door Caroline had it open and was pulling me inside.

"I can't believe this is happening to me." She cried.

"I know. But no matter what's happening you're better than this. If he's cheating on you then he's completely stupid. Now guy with half a brain would ever betray you." I told her and she flung her arms around me again.

"I love you Lena." She cried into my shirt. After she cried for a few minutes she pulled back and wiped all traces of tears from her face.

"Are you okay now?" I asked her carefully.

"I'm sorry I broke down. Will you stay with me?" She asked and I nodded my head.

"We can have a chick flick and junk food night." I told her and she smiled at me.

"That's exactly what I need." She told me and hugged me once more.

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**Damon POV**

After going home for a couple of hours Klaus texted me telling me that all the guys were meeting at the Grill to play pool. It was Mason's birthday tomorrow so he was throwing himself a pre-birthday party tonight. Everyone one we knew would be there and everyone would be getting pissed on a Sunday night. Only Mason would invite everyone to a party where there would most definitely be booze on a Sunday night. I agreed to go only because I knew Elena was spending the evening with Caroline after her revelation about Tyler. I couldn't explain it but I kind of felt protective of the blonde. She was my girls best friend so I tended to worry about her too.

"I'm going out." I called to my dad as I left the house. He said goodbye as I walked out, I knew he was mentally preparing for my mom to come home. She was flying in next week and it took that long to mentally prepare for her arrival. My mom was something else to say the least. I got into my car and drove towards the Grill, when I got there I was shocked at how full the parking lot was already. I also knew that the Grill would stay open late on a Sunday night for Mason. He just had that effect on people. Except Elena that is.

"Dude you made it." Mason clapped me on the shoulder when I walked in.

"Where else would I be?" I asked dryly as I walked in.

"Out tapping that virgin piece of ass?" He asked me and I rolled my eyes. I really didn't want to get into a fight with Mason tonight. I walked over to the bar and ordered myself a beer before sitting down on the stool. I was planning on behaving tonight, I had no intention of going to school with a hangover but I had every intention of going to school to see Elena. I said hi to a few people who were invited by Mason. He invited everyone in our grade and all of the seniors. Along with them he invited a handful of sophomores, just the ones he declared cool enough. He never invited freshman, according to Mason they didn't count until they were at least sophomores unless your name was Jeremy Gilbert. Mason only associated with him for his lunch money. I looked around the place looking for someone I actually wanted to talk to.

"She's not here dude." Klaus said sitting on the stool beside me with a beer in hand.

"Who?" I asked. 

"Elena." Klaus teased.

"I know that, she's with Caroline. She's having boy issues." I told him and Klaus immediately perked up.

"Tyler doesn't deserve a girl like that. He's here flirting and she's at home upset." Klaus muttered.

"Elena's with her. I was actually thinking of calling her and asking her to come." I told him.

"Do it. It'll be good to see you be all twitterpated with Elena." Klaus told me.

"I think it's more so you can eye Caroline all night. But I'll call and ask Elena if she wants to come hang out." I told him pulling my phone out of my pocket and dialling her already familiar cell number. After a short conversation Elena agreed to come and join us here with Caroline. She wanted Caroline to show Tyler that she didn't need him. That he could do what he wanted but she would get the last laugh.

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**Elena POV**

"Are you sure I can face him? Caroline asked me as we walked up to the Grill.

"Absolutely. You don't have to face him, if he's going to cheat it's going to be tonight. Just watch and see what he does. There are a lot of people in here I don't think he'd notice you unless you walked right up to him." I told her and she nodded.

"Alright. Should I flirt with anyone tonight?" She asked.

"No, don't sink down to his level. Don't move on until it's actually over. You don't need him holding flirting over your head too." I told her and she nodded, agreeing my theory made sense.

"You lot hot. Damon isn't going to know what hit him." Caroline told me.

"I just can't believe we're at a party on a Sunday night." I told her giggling. I teetered for an instant in my four inch heels but quickly caught my balance. My combination of white camisole, leather jacket and tight jeans meant that a bunch of guys were already creepily licking their lips.

"No guy can keep their eyes off of you. I wish I had your legs. And ass. Your ass is pretty fantastic. I'd be surprised if Damon doesn't start a fight over you tonight." Caroline said and I brushed her off.

"Well look who it is our favourite virgin." Mason catcalled and I sighed.

"Where's Damon." I asked and he shrugged.

"He's around. But between you and me, you wouldn't be a virgin for much longer if you looked like that." He told me and I rolled my eyes.

"Let's go find Damon." I told Caroline and she nodded. When we walked past Mason she shot up her middle finger at him and I laughed.

We found Damon by the bar with a beer in hand.

"Hey." I greeted him, walking over and kissing him quick.

"Hey baby." He said wrapping his arms around my waist, his hands resting just above my ass.

"Hi. Having fun?" I asked him.

"Not as much as I could be having." He said to me and Caroline chuckled awkwardly.

"Well that's awkward. But on a more important note, look at that jackass. His hand is down the back pocket of that sluts jeans." Caroline ranted.

"He's been doing that all night." Damon told her and she hissed.

"I am this close to breaking up with him." She hissed.

"He wouldn't care until tomorrow. If you're going to do it wait until he's out of here with all these options." Damon told her and she nodded her head thinking he made a good point.

"Caroline gave Mason the finger." I told Damon and he laughed.

"I'm sure he deserved it. By the way you look so hot." He told me and I smiled shyly. I had never had someone appreciate the way I looked so intensely.

"Well thank you. I put this outfit together with you in mind." I told him and he grinned. 

"Wanna dance?" He asked. Somewhere during our conversation I had gotten pulled into his lap. His arms were around my stomach and I was sitting in his lap. It was a very intimate position but I had no issues with that.

"Yeah." I said standing up. Damon stood up too and took my hand lacing our fingers together as he led me onto the floor. His hands immediately went to my hips and knowing what he wanted I started rolling them to the beat of the song. I placed my arms on his shoulders as I moved, his thumbs stoked the sliver to skin that was bared between my camisole and the tops of my low-slung jeans. His hands moved up my sides and I had no idea I knew how to dance like this. It was like it came naturally to me. Our bodies touched and slid against one another and it was getting hot in there. He was hard and I knew it was going to be agony for him.

"God I want you so much. Too much." He told me.

"I want you too. I'm ready. I think I've been ready since yesterday, but I'm really ready now. I don't know what I'm waiting for." I told him and he stared at me.

"You're ready ready?" He asked me.

"Yeah, I want you all the way. I didn't get quite enough last night and I want more. I want all of you, then I'll finally be rid

of my virginity." I told him.

"I don't want that to be the reason we decide to do this." He told me. We'd completely stopped dancing in the middle of the dance floor.

"It's not. I want to be with you. It's all I can think about." I promised him.

"You won't be able to stay out tonight. We have school in the morning." He reminded me.

"It's okay. We can leave now. We can go to your place. When we're done you can take me home." I told him.

"Is that how you want it?" He asked.

"Yes. I want nothing more tonight than for you to make love to me." I told him and he finally nodded.

"How is Caroline getting home?" He asked me.

"We got a ride here from her mom. We can drive her home then go to your house." I told him and he nodded.

"I'll go get the car, you grab Caroline." He told me before leaning down to kiss me. He walked directly to the door and I went to find Caroline who was sitting next to Klaus.

"Damon and I are leaving, do you want a ride home?" I asked her.

"Yeah, I've seen enough." She told me and she followed me out.

"So you two are going to seal the deal aren't you?" She asked when she was in the backseat of the Camaro.

"As a matter of fact, yes." I told her with a grin. Caroline squealed and wrapped her arms around me from behind.

"You have to text me afterwards with all the details." She said and Damon rolled his eyes.

"We'll see." I said.

"You have to. Best friend law." She informed me and I chuckled. By now Damon had parked in front of her house and I let her out.

"We'll see. I'll call you when I get home." I told her and she hugged me before walking up to her house. Once she was gone I got back into the car and we drove the rest of the way to his house.

When we got there we snuck upstairs not wanting to meet up with any of his family.

"You can still change your mind. We don't have to do this." He told me.

"I want to." I told him as we entered his bedroom.

"If it's what you really want." He acquiesced.

"You have no idea." I said and he laughed somewhat nervously. I knew he'd done this before, I just wasn't sure why he was

acting so nervous. He closed his door behind him and walked over to me.

"I'm going to try really hard not to hurt you." He told me and I reached up and kissed him.

"I expect some pain. I know it's going to be there." I told him.

"I don't want to hurt you. I'll go slow and make sure you're ready before I start." He said. I nodded my head but I wasn't scared. He seemed more afraid than I was.

"Are you okay?" I asked him.

"It's going to actually mean something this time. I've never been with someone who I actually care about before." He told me and I smiled at him.

"So this is a first for both of us in a way." I told him and he nodded his head.

"Yes, in a way it is." He agreed. Deciding that I needed to make the first move since he seemed resistant I pulled my shirt over my head. I didn't have that much time, I needed him to get moving. I didn't want my first time to be rushed. He groaned and took a couple of steps towards me, kissing me deeply. His tongue broke through the seam of my lips and I willingly kissed him back just as intensely. I felt us backing towards the bed and whine my knees hit the back of it I slid back with him helping me. He followed me onto the bed as he slid us across the bed together, never once breaking our kiss. He pulled his shirt off as we moved across the bed and dropped it on the floor. He didn't really care where it landed, it was just laundry he could pick it up later.

"You need to tell me before we get too far if you want to stop." He told me and I nodded. I didn't want to stop, I was sure that nothing could make me want to stop. When he was lying along my body I reached in between us to undo his pants. I wanted him to know that I wasn't afraid and I wanted to do this. I was so excited and so turned on that I was sure I wasn't going to be able to wait too long. He pulled back to let me remove his pants all the way along with his underwear. Now he was completely naked and I swear I've never seen anything more beautiful.

"I want you. All of you." I told him never having been more serious about anything my whole life. I wanted this and I wanted it now. He leaned in and kissed me instead of answering which was fine by me. I wasn't nervous at all, it felt like it was meant to be happening here and now.

"I'll be careful." He whispered before sliding his hand down my body. I gasped when his two of his fingers slipped inside me. It felt heavenly but that wasn't what I wanted inside me.

"Damon..." I pleaded, needing more than what he was giving me. He widened his fingers stretching me and I knew he was trying to make it more comfortable for me when he replaced his fingers with a different appendage.

"Patience baby. I don't want to hurt you." He told me and I nodded. His desire to not hurt me was far too much for me to bear. He was so tender with me, nothing like I imagined having sex with him to be like. When he pulled his fingers out he leaned down and kissed me once more before lining his erection up with me. I took a deep breath as he slowly starting sliding inside of me. He moved slowly always stopping every couple of inches to make sure I was okay. This was exactly what I needed.

"Okay, this is the part that's going to hurt a little." He told me and I nodded my head, mentally prepared for it. I welcomed the pain because then I would be fully joined with him. It was all I could think about. When he pushed past that final barrier I gasped because the pain was more than I expected. The pain quickly subsided as he stayed still not moving until I felt good enough for him to.

"Are you okay?" He asked me softly. He was bracing his weight up on his arms so he didn't crush me. I was amazed at how caring he was being. This was nothing like I imagined before I got to know him.

"Please move. I need more." I told him and he smiled leaning down to capture my lips between his. He kissed me thoroughly as his body started slowly moving against me. It didn't take long for me to start enjoying this as much as he was. It felt amazing and I was suddenly sure that this is what actually making love felt like. Damon was making love to me. It wasn't just sex, this was love and love was exactly what I was feeling for him. I was in love for the first time. I had a hard time keeping my eyes open with the feelings he was evoking in me. I wanted to stare into his baby blues but I couldn't. I didn't move, I let him take the reins on this. He would slide partially out of me before sliding back in at the most tender speed I could imagine.

"How are you doing?" He asked. He never stopped asking me if I was okay. It just seemed to make me love him even more. I nodded my head and he kept moving, his body clenching on every thrust.

"I'm close." I told him, my body clenching with every thrust he made into me.

"Come on baby." He urged me. He wanted me to come and I wanted him to come. I wanted us to come together if that was possible.

"Come with me." I told him and he groaned, dropping his head into my neck. He lifted enough to kiss my lips as he never missed a beat with his lower body. I trailed my hands all over his back, loving the feeling of his skin under my fingertips. His pace quickened to an almost frantic speed, but still he never hurt me. I loved this new speed he had adopted. He only thrust three more times before I came loudly. I shut my eyes and opened my mouth unable to identify the sounds that came out. He followed right behind me and his entire body shook with the force of his orgasm. When he stopped he rolled off of me and pulled me into his arms.

"Best. I. Ever. Had." He informed me while he held me tight against his chest.

"Really?" I asked certain he was lying.

"It's never felt like that for me." He told me. I smiled but glanced at the clock.

"I really don't want to but if I don't want to miss curfew then we should probably get me home." I sighed dismally.

"Okay." He said unwinding himself from me and pulling his pants back on. He picked up all of my clothes and I redressed quickly.

Once we were both done I followed him downstairs and out to his car.

"You have no idea how badly I want to stay." I told him once I was buckled into the passenger seat.

"You have no idea how badly I want you to stay. But it's okay, I want your parents to like me so they'll let me be with you more often." He told me and I smiled.

"It'll take some time but they'll approve eventually." I told him and he leaned over the console to kiss me. I kissed him back but pulled away far earlier than I wanted to.

"Better get you home." I said as he drove away from his house. When we got to my house he parked the car and leaned over and kissed me again.

"Do you want me to walk you to your door?" He asked.

"Better not, I don't need any more questions. After-all I'm supposed to be with Caroline." I told him and he chuckled.

"Rebellious Elena. Lying to her parents so she can have sex with her boyfriend." He teased.

"Shut up, that's not how it went at all if you remember correctly." I laughed.

"Right, of course. I guess I'll see you at school tomorrow. Do you want a ride?" He asked me and I nodded enthusiastically.

"You bet I do. More time to spend with my amazing boyfriend." I told him.

"Okay, I'll see you bright and early tomorrow morning." He told me and I nodded.

"One more thing before I go inside." I told him before leaning in and kissing him. He kissed me back before we mutually pulled away. I got out of the car and watched him drive away knowing that tonight was one of those nights I was never going to forget.


	11. Pretending

**Another shorter one but I had to cut it in half. It was far too long, the next one will be longer. A wee little bit of drama in this one but that will be over next chapter. Enjoy and let me know what you think as always. Thank you for turning this into such a popular story. **

* * *

**Elena POV**

"Good morning sweetheart." My dad greeted me when I walked into the kitchen the next morning.

"Good morning daddy." I greeted him leaning down to kiss his cheek.

"What's got you in such a good mood this morning?" I asked staring at me suspiciously. I was never in this kind of mood first thing in the morning. I wasn't usually a morning person, but if the morning was when I was able to see Damon then it is what it is. I officially loved mornings because Damon would be there when I got to school.

"I don't know. I guess I just slept really good last night." I shrugged. There was no way I was divulging to my father that I lost my virginity last night and I was so happy. That was no conversation I wanted to have. No way in hell. Maybe with almost anyone other than my dad.

"Well I'm glad to see it. Do you need a ride to school or is Damon picking you up?" My dad asked. He was trying really hard to tolerate my relationship with Damon but I could tell he didn't like it.

"Actually Caroline's mom is giving us a ride. She doesn't want to go to school alone just in case Tyler comes up to her. They're on the outs right now and she doesn't want to talk to him alone." I answered.

"Sounds good. Do you need a ride home?" He asked.

"I'm not too sure yet. Depends on if Damon wants to hang out after school. I need to ask him to help me with my calculus homework sometime since he's practically acing the class and I'm struggling." I told him.

"That's a good idea." My dad agreed and I smiled. I couldn't stop smiling this morning and I knew exactly why.

"What are you smiling about?" My mom asked when she came into the room a few minutes later with her robe on and her hair tied up. My mom wasn't a morning person either, but she refused to stay in bed when her kids were out of it. She never had and never would until we were moved out.

"I'm just in a really good mood." I told her and my dad shrugged and shook his head. He grabbed his briefcase and kissed my mom before walking out the front door.

"Now why are you really smiling? Your dad is gone and Jeremy has been gone for a while. I have no idea where he goes but at least I'm fairly confident he's not getting into trouble." My mom asked me with a knowing smile on her face.

"I don't know. I'm just happy." I told her.

"Does it have something to do with Damon?" My mom asked with her small smile on her face. I knew exactly what that smile meant and I knew she was on to me.

"Yes." I answered, refusing to give too much away.

"Did he tell you he loved you? Because if he did you should know that it's very soon and be careful." My mom asked.

"No that hasn't happened. I don't expect it to anytime soon, he's not accustomed to feeling like that and he told me that he would probably screw up a few times. He has no idea how to be in a relationship but he's doing so good so far." I told my mom.

"Do you love him?" She asked me and I smiled shyly.

"I'm so in love with him and I know it's fast. I just couldn't help how my heart feels." I told her.

"Just be careful. You don't want to have differing feelings in the relationship. You don't want to feel too much and him not feel enough." She told me and I nodded. I understood what she meant but I felt confident that Damon cared about me and I was sure he would grow to love me sometime too.

"I know." I told her.

"And just be careful when the sex issue comes up. Make sure both your head and your heart agree that it's the right thing to do." My mom told me.

"Um... I did. Both my heart and my head told me it was time." I admitted and my moms eyes went wide.

"You don't want to regret your first time. It's the most important time." My mom reminded me.

"I don't regret it. Sex is something people do when they're in love." I told my mom and she nodded.

"He didn't pressure you did he?" She asked still worried..

"No, it was my idea. I wanted it and he asked me if I was sure so many times before it actually happened. He was so gentle." I told her when I heard the car honk outside. "There's Caroline." I told her and my mom nodded. She didn't seem worried anymore which I was happy about.

"Alright, I'll see you after school." She told me and I nodded.

When I got into Caroline's mom's car, Caroline turned around and gave me a look that meant we would be having a talk when we got to school. I knew she was going to ask me about last night. I fully expected her to and I knew exactly what I was going to tell her.

"Good morning Elena." Sheriff Forbes greeted me and I smiled back. Once I was buckled in she started driving. The second we got to school and we got out of the car Caroline was staring at me expectantly.

"Well? How was it?" She asked me and I sighed.

"It was wonderful." I told her.

"Was he tender, or did he just get it over with?" She asked.

"He was so gentle with me. It was so and so beautiful." I told her.

"I'm so happy for you." Caroline squealed as we walked to our table. She glared when she saw Tyler sitting with Mason and Klaus. Damon hadn't come to school yet.

"Are you going to break up with him?" I asked her.

"I don't know yet. I guess we'll find out today. I want to I just don't want to be alone." Caroline said.

"It's better to be alone than with a cheater." I told her certainly.

"I know that. It's just we've been together for so long now that it's hard to end it." Caroline sighed.

"I know. But you have to think about yourself too. It's not good for you to be in a relationship like that." I told her and she

nodded.

"I do know that, it's just that I hate change." She said and I nodded, understanding where she was coming from.

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**Damon POV**

I pulled into the school parking lot with a smile on my face. It wasn't too often that I was happy about going to school. But today I was, I couldn't wait to see my gorgeous girlfriend who was escalating into goddess territory in my books. I saw her sitting with Caroline and I waved and she grinned back. I went to my table and sat my bag down on the table.

"What did you do this weekend? I never saw you?" Mason asked. Tyler was sitting beside him and Klaus was beside me. The rest of the group wasn't here and I didn't really care.

"Spent it with Elena." I said and Klaus looked at me with a knowing smirk on his face.

"Oh did Little Miss Good Girl finally give it up?" He asked chuckling.

"Not that it's any of your business but yes. We're not talking about it, it doesn't concern you." I told him.

"Ooh so it seems I owe you twenty bucks. I'll bring it at lunch." He told me and I rolled my eyes. It was so not about the bet anymore. It hadn't been for a long time. But Mason was never going to let it go.

"I don't want your money. I have plenty of my own." I told him.

"I always pay my debts." He told me and I rolled my eyes.

"Just let it go." Klaus advised and I nodded. It was best not to sink to Mason's level. We were friends of convenience, not because we actually liked each other. When the bell rang I grabbed my bag and started walking to class with Klaus beside me. We were in most of the same classes which was great.

The morning went by so slow, when the lunch bell finally rang Klaus and I walked out.

"So did Mama Mikealson pack me food or am I buying a lunch?" I asked as we stopped at Klaus's locker to get his lunch.

"What do you think? You're more my brother than my real brothers are. Mama recognizes that." He said and I fist pumped. Mama Mikealson's lunches were the best ever. On our way out to the table, Elena intercepted me.

"Hey." She greeted.

"Hey." I said back lowering my head to kiss her quickly.

"I thought I'd come sit with you today." She told me and I smiled at her.

"Sure." I told her taking her hand in mine. I just hoped Mason would keep his mouth shut. She didn't need to know about the bet. Not now that things were going to so well for us.

"Good on your for taming my friend." Klaus told her and she smiled at him.

"It was all him." She told him.

"It definitely was all you. He's a lot more likeable now." Klaus said and Elena laughed.

Lunch was going well until Mason showed up with a to Mystic Grill to-go bag.

"I had to buy lunch so I could get the cash I owe you." He said sending the twenty across the table to me.

"It's not necessary Mason. I don't want it." I told him hoping he'd get the point.

"Nah, you won the bet fair and square." He said pushing it back across. I pushed the money back with a glare. He would ruin everything.

"What bet?" Elena asked interested.

"It's nothing." I told her hoping Mason would leave it be.

"Mason stop." Klaus interjected.

"Why, the girl asked what the bet was about. I think she deserves to know." He said.

"Mason..." I warned him.

"I owe Damon twenty bucks because he managed to sleep with you before I did." Mason said vindictively.

"What is he talking about?" Elena asked.

"He's just talking about shit that he doesn't understand." I assured her trying to stop this before it got out of hand.

"I understand just fine. We put twenty bucks on the line for the guy that popped Elena Gilbert's cherry first." Mason laughed. I watched in horror as Elena's face went bright red and then completely pale as all the blood drained. She looked ashen like the worst thing she could imagine happened.

"Is this true?" She asked me.

"Elena..." I started. Mason had a grin on his face, I could see this being like watching a car accident unfold for him. He was completely intrigued. Klaus was sitting there like he didn't know what he should do. There really wasn't anything he could do.

"No, just answer the question. Did you and Mason make a bet about you could sleep with me first?" She asked me.

"It's not as easy as that." I insisted.

"Oh it's not? Just answer the question Damon? Yes or no?" She demanded. She looked ready to bolt. I was going to kill Mason.

"Technically yes. But it's not like he said." I told her.

"Oh it's not? What was it then?" She demanded. She wasn't really listening. She was running on pure emotion.

"The bet wasn't valid anymore. It stopped when it didn't work out the first time." I told her and she laughed dryly.

"You think that makes it better? You made a bet with your friend for who can sleep with me first. Well good work, you succeeded. I guess that means everything is done." She told me getting up and stepping over the bench.

"No it's not." I told he standing up.

"Don't make a scene Damon. I don't want this going over the entire school. Just leave me alone. You won your bet, you

should just be able to walk away now." She told me.

"I can't just walk away. Things changed when you broke up with me the first time." I told her.

"I thought things had changed, but apparently they haven't. Just leave me alone. Whatever I thought we had was a lie. It just sucks that I had to fall in love with you before I realized what an asshole you are." She said sadly. I stepped over the bench to try to follow after her but she spun around on her heel to stare at me. She had her hands out in front of her in a defensive position and I stopped.

"Elena, can we just talk? We can go to my car and talk about this?" I asked her. No one was looking at us which was good aside from Mason, Klaus, Tyler and Caroline. She didn't want to cause a scene and we weren't so far.

"No, I don't' want to talk to you. I don't want to see you." She told me. Her words cut deep and I tried to go after her again.

"Elena don't. It wasn't like that." I promised her.

"It doesn't matter Damon. You got what you wanted. You were my first. You know what, my mom told me this morning that she didn't want me to regret my first time because nothing it worse than that. She was right. I regret it and nothing feels worse." She told me before spinning on her heel and walked away. I decided I needed to give her a little time, she didn't want to make a scene.

"Well that was dramatic." Mason whistled. Tyler sat silently beside Mason not sure how he felt about what just happened.

"You're an asshole Mason." I told him not having any words at the moment that conveyed how I felt.

"I was just being honest Damon." Mason said.

"You just can't stand someone else winning, can you? You lost Mason. You just can't stand that." I said to him.

"It's not my fault you just lost her." Mason said sounding bored. Mason was partially right, it wasn't entirely his fault. I should have been honest with her from the beginning. At the beginning I told her about a bet but I didn't tell her that it was about sex. I should have from the beginning but I didn't. It was the worst mistake I've ever made.

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**Elena POV**

I walked back over to my table intending to just tell Caroline that I was signing out and going home.

"Are you okay?" She asked me.

"I'm hurt, I'm pissed and I'm completely regretting last night. I have to go." I told her.

"What happened?" She asked.

"He had a bet going with Mason about which of them could sleep with me first. None of it was real. I fell in love with him

and he was just pretending." I told her.

"I'm sorry." Caroline said rubbing my arm soothingly.

"It's okay. I'll be fine. I just have to go home." I told her and she nodded.

"Are you going to call for a ride?" She asked.

"No, I need some time to get my emotions in check. I don't want my mom to worry about me. I just hate that she was so right." I said. Caroline nodded and stood up to hug me. Out of the corner of my eye I saw her shoot the middle finger towards Damon's table. That was the kind of friend Caroline Forbes was. She would go to battle with anyone who hurt me and I for her.

"Alright. Call me if you need anything." She told me and I nodded.

"I will. You're the first person I call." I promised and she hugged me. I slung my backpack over my shoulder and grabbed my slice of pizza before walking towards the office. I sighed out quickly then fled the school.

When I got home my mom was sitting at the table doing a crossword puzzle.

"What are you doing home?" She asked me.

"I wasn't feeling good." I lied.

"Oh, you should have called me to come and pick you up." She said feeling my forehead.

"I needed to walk. The air felt good." I told her truthfully. The walk home was good for me.

"Okay, you should go lie down." She told me. I nodded and did what she said. The day was only half over but I wanted it to end right now. I was so ready for the entire day to be over. I wished it was possible to do a rewrite. I would have changed everything that happened over the past few weeks. But it was impossible so I just had to sit here and endure it. It was going to get worse before it got better. But someday I would get over him and everything to do with him. I shut the door to my bedroom and threw the flowers he got me into the trash. One less thing to remind me of him.


End file.
